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1,2,3-Benzotriazole
N,N-dimethyl-formamide dimethyl acetal
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 90℃; for 4h; | 87.8% |
methyl magnesium iodide
1-(chloromethyl)-1H-benzotriazole
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
1-ethylbenzotriazole
Conditions | Yield |
---|---|
In diethyl ether for 1h; Ambient temperature; | A 83% B 11% |
1,2,3-Benzotriazole
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 5℃; for 1h; Alkylation; | 80% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetonitrile for 48h; | 73% |
With potassium tert-butylate; 18-crown-6 ether In diethyl ether for 1h; Ambient temperature; | 70% |
Stage #1: 1,2,3-Benzotriazole With sodium hydride In tetrahydrofuran; mineral oil for 0.0833333h; Stage #2: With carbon disulfide In tetrahydrofuran; mineral oil at 0 - 5℃; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0 - 5℃; for 0.2h; | 67% |
With sodium hydroxide In water; acetonitrile at 20℃; for 48h; | 55% |
1H-benzotriazole-1-carboxylic acid methyl ester
A
2-methylbenzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
at 120℃; Title compound not separated from byproducts; | A 29% B 71% |
at 160℃; | |
at 160℃; | |
at 120℃; Mechanism; other alkoxycarbonylbenzotriazoles; | A 29 % Spectr. B 71 % Spectr. |
1-benzyl-3-methylbenzotriazolium iodide
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
(E)-1,2-diphenyl-ethene
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 20℃; stereoselective reaction; | A n/a B 68% |
N-chlorobenzotriazole
A
1,2,3-Benzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
C
1-iodobenzotriazole
Conditions | Yield |
---|---|
With methyl iodide In dichloromethane at 42℃; for 1h; | A 10% B 6% C 65% D 19% |
With methyl iodide In dichloromethane at 42℃; for 3h; | A 18% B 11% C 41% D 30% |
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 2.5h; | 65% |
With sodium hydroxide In water at 20 - 80℃; for 0.75h; |
N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide
benzylmagnesium chloride
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
1-phenethyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 45℃; for 3h; | A n/a B 64% |
N-methyl-1,2-phenylenediamine
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; nitromethane; caesium carbonate; acetic acid; potassium iodide In water at 120℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 62% |
With hydrogenchloride Diazotization.und Verkochen das entstandende Diazoniumsalz; |
1,2,3-Benzotriazole
methyl iodide
A
2-methylbenzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; | A 40% B 60% |
With potassium hydroxide; tetrabutylammomium bromide at 0℃; Yields of byproduct given; | A 25% B n/a |
With sodium hydroxide In N,N-dimethyl-formamide for 0.25h; Ambient temperature; Yield given. Yields of byproduct given; | |
With potassium hydroxide; tetrabutylammomium bromide Ambient temperature; Irradiation; Yield given. Yields of byproduct given; | |
With potassium hydroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 2h; |
Dimethyl oxalate
1,2,3-Benzotriazole
A
2-methylbenzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide Heating; | A 35% B 59% |
With potassium tert-butylate In N,N-dimethyl-formamide for 3h; Heating; | A 35% B 59% |
With potassium tert-butylate In N,N-dimethyl-formamide for 3h; Heating; | A 35% B 59% |
N,N-dimethyl-2-nitro-benzenamine
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
N-nitroso N-methyl-N-(2-nitroaniline)
C
N-methyl-N-nitrosoaniline
D
2-nitro-N-methylaniline
Conditions | Yield |
---|---|
With n-Butyl nitrite; ammonium chloride; water for 2h; Heating; Further byproducts given; | A 7% B 58% C 9% D 5% |
N,N-dimethyl-2-nitro-benzenamine
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
N-nitroso N-methyl-N-(2-nitroaniline)
C
2-nitro-N-methylaniline
D
nitrobenzene
Conditions | Yield |
---|---|
With n-Butyl nitrite; ammonium chloride; water for 2h; Mechanism; Heating; | A 7% B 58% C 5% D 1% |
1-benzyl-3-methylbenzotriazolium bromide
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
(E)-1,2-diphenyl-ethene
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 20℃; stereoselective reaction; | A n/a B 56% |
N-chlorobenzotriazole
methyl iodide
A
1,2,3-Benzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
C
1-iodobenzotriazole
Conditions | Yield |
---|---|
In dichloromethane at 42℃; for 7h; | A 8% B 21% C 16% D 55% |
In dichloromethane at 42℃; for 5h; | A 8% B 28% C 29% D 35% |
N-chlorobenzotriazole
methyl iodide
A
1,2,3-Benzotriazole
B
2-methylbenzotriazole
C
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In dichloromethane at 42℃; for 3h; Further byproducts given; | A 8% B 3% C 33% D 49% |
(E)-benzotriazole-1-carbaldehyde oxime
methyl iodide
A
2-methylbenzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 25℃; for 24h; | A 12% B 42% C 26% |
tert.-butylhydroperoxide
1,2,3-Benzotriazole
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In water; acetonitrile at 100℃; for 8h; Schlenk technique; Inert atmosphere; regioselective reaction; | 42% |
1,2,3-Benzotriazole
N,N-dimethyl-formamide dimethyl acetal
A
2-methylbenzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In toluene for 0.5h; Heating; | A 38% B 10% |
N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
1-[(1H-benzotriazol-1-yl)methyl]-1H-benzotriazole
Conditions | Yield |
---|---|
In diphenylether at 200℃; for 2h; | A 15% B 38% |
N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide
N,N-diethylaniline
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
1-ethylbenzotriazole
C
1-[(1H-benzotriazol-1-yl)methyl]-1H-benzotriazole
Conditions | Yield |
---|---|
at 200℃; for 4h; | A 8% B 37% C 28% |
N-bromobenzotriazole
methyl iodide
A
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In dichloromethane at 42℃; for 3h; | A 26% B 35% |
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 70℃; for 90h; | 32% |
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
N-methyl-N-phenylformamide
Conditions | Yield |
---|---|
With lead(IV) acetate In methanol for 0.5h; Ambient temperature; | A 20.2% B 17.2% |
2-Chloronitrobenzene
methylhydrazine
A
1-methyl-1H-benzo[d][1,2,3]triazole
B
3-methyl-3H-1,2,3-benzotriazole 1-oxide
C
2-nitro-N-methylaniline
D
2-Chloroaniline
Conditions | Yield |
---|---|
In ethanol at 150℃; for 5h; | A 12% B n/a C n/a D 20% |
1-iodobenzotriazole
methyl iodide
A
1,2,3-Benzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In dichloromethane at 42℃; for 3h; | A 10% B 10% C 12% |
1-iodobenzotriazole
A
1,2,3-Benzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With methyl iodide In dichloromethane at 42℃; for 3h; | A 10% B 10% C 12% |
diazomethane
1,2,3-Benzotriazole
A
2-methylbenzotriazole
B
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With ethanol |
1-(chloromethyl)-1H-benzotriazole
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | |
Multi-step reaction with 2 steps 1: 40 percent / methanol / 1 h / Heating 2: toluene; diethyl ether / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 87 percent / toluene; methanol / 2 h / Heating 2: benzene; diethyl ether / Heating View Scheme |
1-methyl-1H-benzo[d][1,2,3]triazole
borane-THF
N-1-methyl-benzotriazole-N-3-borane
Conditions | Yield |
---|---|
In not given (C6H4N3)Me (1.1 equiv.), 1.0 M BH3*THF (1.0 equiv.), room temp.; | 99% |
In tetrahydrofuran for 2h; Cooling with ice; | 84% |
1-methyl-1H-benzo[d][1,2,3]triazole
N-1-methyl-benzotriazole-N-3-borane
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 20℃; Inert atmosphere; | 99% |
1-methyl-1H-benzo[d][1,2,3]triazole
silver trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; | 97% |
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With triethyl orthoformate In ethanol to a soln. of NiCl2*6H2O in abs. ethanol was added CH(OEt)3, refluxed for 30 min, addn. of the triazole (molar ratio 1:1); filtered, washed with ethanol and Et2O, dried in vac. over silica gel; elem. anal.; | 96% |
1-methyl-1H-benzo[d][1,2,3]triazole
(Br2)(1-methylbenzotriazolyl)2cobalt(II)
Conditions | Yield |
---|---|
In ethanol dropwise addn. of CoBr2 in absolute EtOH to a stirred solution of ligand in absolute EtOH (under aerobic conditions), forming ppt., further stirring for 30 min; filtn., washing with EtOH and diethyl ether, drying in vacuo over silica gel, elem. anal.; | 95% |
1-methyl-1H-benzo[d][1,2,3]triazole
phenanthridine
propynoic acid methyl ester
Conditions | Yield |
---|---|
In dichloromethane at -10 - 20℃; | 91% |
1-methyl-1H-benzo[d][1,2,3]triazole
3-methyl-3H-1,2,3-benzotriazole 1-oxide
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In dichloromethane at 20℃; for 24h; | 90% |
1-methyl-1H-benzo[d][1,2,3]triazole
phenanthridine
propynoic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at -10 - 20℃; | 90% |
1-methyl-1H-benzo[d][1,2,3]triazole
1,3,5-triphenylhexahydro-1,3,5-triazine
Conditions | Yield |
---|---|
at 700℃; under 0.01 Torr; Elimination; Cyclotrimerization; | 89% |
1-methyl-1H-benzo[d][1,2,3]triazole
(MebtaH)((chloro)3(1-methylbenzotriazolyl)cobaltate(II))
Conditions | Yield |
---|---|
With concd. HCl In ethanol addn. of CoCl2*6H2O in concd. HCl-EtOH to a stirred soln. of ligand in concd. HCl-EtOH (under aerobic conditions), formation of ppt.; filtn., washing with EtOH and diethyl ether, drying in vacuo over silica gel, elem. anal.; | 89% |
4-methyl-benzoic acid methyl ester
1-methyl-1H-benzo[d][1,2,3]triazole
2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)-1-ethanone
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h; | 88% |
1-methyl-1H-benzo[d][1,2,3]triazole
Methyl decanoate
1-Benzotriazol-1-yl-undecan-2-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h; | 88% |
1-methyl-1H-benzo[d][1,2,3]triazole
copper(ll) bromide
CuBr2(C6H4N3CH3)
Conditions | Yield |
---|---|
In acetone room temp. (overnight); filtering, washing (Me2CO, Et2O), drying (vac., over SiO2); elem. anal.; | 88% |
1-methyl-1H-benzo[d][1,2,3]triazole
2-methylmercaptobenzothiazole
1-(1,3-Benzothiazol-2-ylmethyl)-1H-1,2,3-benzotriazole
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 24h; | 85% |
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With triethyl orthoformate In ethanol to a soln. of NiCl2*6H2O in abs. ethanol was added CH(OEt)3, refluxed for 30 min, addn. of the triazole (molar ratio 1:2); filtered, washed with ethanol and Et2O, dried in vac. over silica gel; elem. anal.; | 85% |
1-methyl-1H-benzo[d][1,2,3]triazole
cobalt(II) thiocyanate
(cobalt(isothiocyanate)2(1-methylbenzotriazole)2)
Conditions | Yield |
---|---|
In acetone addn. of solid ligand to a stirred soln. of Co(NCS)2 in acetone (under aerobic conditions), stirring for 10 min at room temp.; filtn., addn. of n-hexane to the filtrate to yield dark blue oil, solidification on overnight storage in a freezer, collection by filtn., washing with n-hexane, drying in vacuo over silica gel, elem. anal.; | 84% |
1-methyl-1H-benzo[d][1,2,3]triazole
ethyl pelargonate
1-Benzotriazol-1-yl-decan-2-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h; | 83% |
1-methyl-1H-benzo[d][1,2,3]triazole
cobalt(II) chloride
(chloro)2(1-methylbenzotriazolyl)2cobalt(II)
Conditions | Yield |
---|---|
In ethanol dropwise addn. of CoCl2 in absolute EtOH to a stirred solution of ligand in absolute EtOH (under aerobic conditions), forming ppt., further stirring for 30 min; filtn., washing with EtOH and diethyl ether, drying in vacuo over silica gel, elem. anal.; | 83% |
1-methyl-1H-benzo[d][1,2,3]triazole
α-bromoacetophenone
3-methyl-1-phenacylbenzotriazolium bromide
Conditions | Yield |
---|---|
In toluene for 5h; Heating; | 80% |
In ethyl acetate for 3h; Heating; | 72% |
1-methyl-1H-benzo[d][1,2,3]triazole
nickel(II) thiocyanate
Ni(NCS)2(CH3OH)2(C6N3H4CH3)2
Conditions | Yield |
---|---|
With methanol In methanol the triazole was dissolved with stirring in a soln. of Ni(SCN)2 in refluxing methanol, left undisturbed at ambient temp.; filtered, washed with Et2O, dried in air; elem. anal.; | 80% |
Conditions | Yield |
---|---|
With HC(OEt)3 In ethanol dissoln. of equimolar amts. of CuCl2 and ligand in EtOH contg. HC(COEt)3; crystn. (2 d, room temp.), filtration, washing (Et2O), drying (vac.); elem. anal.; | 80% |
1-methyl-1H-benzo[d][1,2,3]triazole
Ethyl hexanoate
1-(1H-1,2,3-benzotriazol-1-yl)-2-heptanone
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h; | 78% |
1-methyl-1H-benzo[d][1,2,3]triazole
Ni(NO3)2(C6N3H4CH3)4
Conditions | Yield |
---|---|
With triethyl orthoformate In ethanol to a soln. of the triazole in abs. ethanol was added a soln. of Ni(NO3)2*6H2O in the same solvent, addn. of CH(OEt)3, refluxed for 30 min; addn. of Et2O to the cooled soln., filtered, washed with Et2O, dried in vac. over silica gel; elem. anal.; | 78% |
1-methyl-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
In dichloromethane for 144h; Ambient temperature; | 77% |
1-methyl-1H-benzo[d][1,2,3]triazole
silver trifluoromethanesulfonate
triazole
Conditions | Yield |
---|---|
Stage #1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In methanol for 0.0833333h; Inert atmosphere; Stage #2: 1-methyl-1H-benzo[d][1,2,3]triazole In methanol at 20℃; for 12h; Inert atmosphere; | 76% |
byproducts: AgCl; |
1-methyl-1H-benzo[d][1,2,3]triazole
acetonitrile
copper(ll) bromide
CuBr2(C6H4N3CH3)2(CH3CN)
Conditions | Yield |
---|---|
In acetonitrile room temp. (24 h); filtering, washing (Et2O), drying; elem. anal.; | 75% |
1-methyl-1H-benzo[d][1,2,3]triazole
NiBr2(CH3OH)2(C6N3H4CH3)2
Conditions | Yield |
---|---|
With triethyl orthoformate In methanol to a stirred soln. of NiBr2*3H2O in abs. methanol were added CH(OEt)3 and a soln. of the triazole in abs. methanol, refluxed for 30 min; layered with Et2O at 4°C, slow mixing, filtered, washed with Et2O, dried in air; elem. anal.; | 74% |
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