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5-[[(2-acetamidoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
In water for 2.5h; Reflux; Alkaline conditions; | 98% |
With water; sodium hydroxide for 2.5h; Reflux; | 98% |
With sodium hydroxide In water for 2h; Reflux; | 94% |
(5-dimethylaminomethyl-furan-2-yl)-methanol
2-mercaptoethylamine hydrochloride
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
With hydrogenchloride; hydroquinone at 0℃; for 20h; | 72% |
In hydrogenchloride | 56% |
In methanol at 120 - 130℃; for 7h; |
2-chloroethanamine hydrochloride
2-(N,N-dimethylaminomethyl)furyl-5-(methylthiosulfonic) acid
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile for 5h; Ambient temperature; | 65% |
2-aminoethylthiosulfonic acid
5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
With hydrogenchloride 1.) from 50 to 60 deg C, 2 h, 2.) RT, 16 h; Yield given. Multistep reaction; |
ranitidine hydrochloride
A
N-methylnitroacetamide
B
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
D
methylamine
Conditions | Yield |
---|---|
With sodium hydroxide In water for 4h; Heating; | A 270 mg B 400 mg C 840 mg D 100 mg |
With sodium hydroxide In water for 4h; Mechanism; Product distribution; Ambient temperature; Heating; pH > 9; | A 270 mg B 400 mg C 840 mg D 100 mg |
(2-furyl)methyl alcohol
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / ethanol / 10 h / Heating 2: 72 percent / conc. HCl, hydroquinone / 20 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: methanol / 12 h / 70 - 80 °C 2: methanol / 7 h / 120 - 130 °C View Scheme | |
Multi-step reaction with 2 steps 1: 2.5 h / 90 °C 2: hydrogenchloride / 12 h / 0 - 20 °C View Scheme |
5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91.5 percent / aq. sodium thiosulfate, NaOH / 1 h / 30 °C 2: 65 percent / 50percent aq. NaOH / triethylbenzylammonium chloride / acetonitrile / 5 h / Ambient temperature View Scheme |
5-chloromethylfurfural
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: methanol / 1 h / 20 °C 2.2: 0.58 h / 0 - 20 °C 3.1: sodium hydroxide / water / 2 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: methanol / 0.67 h / 20 °C 2.2: 0.33 h / 0 °C 3.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / Schlenk technique; Inert atmosphere 1.2: 20 °C / Schlenk technique; Inert atmosphere 2.1: methanol / 0.67 h / 20 °C / Inert atmosphere 2.2: 0.33 h / 0 °C / Inert atmosphere 3.1: sodium hydroxide; water / 2.5 h / Reflux View Scheme |
5-[[(2-acetamidoethyl)thio]methyl]furfural
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: methanol / 1 h / 20 °C 1.2: 0.58 h / 0 - 20 °C 2.1: sodium hydroxide / water / 2 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: methanol / 0.67 h / 20 °C 1.2: 0.33 h / 0 °C 2.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme | |
Multi-step reaction with 2 steps 1.1: methanol / 0.67 h / 20 °C / Inert atmosphere 1.2: 0.33 h / 0 °C / Inert atmosphere 2.1: sodium hydroxide; water / 2.5 h / Reflux View Scheme |
5-hydroxymethyl-2-furfuraldehyde
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride / dichloromethane / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: methanol / 0.67 h / 20 °C 3.2: 0.33 h / 0 °C 4.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride / dichloromethane; water / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere 3.1: methanol / 0.67 h / 20 °C / Inert atmosphere 3.2: 0.33 h / 0 °C / Inert atmosphere 4.1: sodium hydroxide; water / 2.5 h / Reflux View Scheme |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 1-butyl-3-methylimidazolium chloride; sulfuric acid / 60 °C 2.1: hydrogenchloride / dichloromethane / 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere 3.2: 20 °C / Inert atmosphere 4.1: methanol / 0.67 h / 20 °C 4.2: 0.33 h / 0 °C 5.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme |
(5-dimethylaminomethyl-furan-2-yl)-methanol
Cysteamine
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
With hydrogenchloride at 0 - 20℃; for 12h; |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With triethylamine In 1,2-dichloro-ethane at 20℃; for 3h; Inert atmosphere; | 98% |
With pyridine In dichloromethane at 0℃; for 3h; | 10.9% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
3-(methylthio)thieno<3,4-d>isothiazole 1,1-dioxide
N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]-thio]ethyl]thieno[3,4-d]isothiazol-3-amine 1,1-dioxide
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 96% |
di-tert-butyl dicarbonate
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
tert-butyl (2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)carbamate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere; | 95% |
With dmap; triethylamine In dichloromethane for 12h; Ambient temperature; | 50% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
(1-adamantyl)methyl isocyanate
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere; | 94% |
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Ranitidine
Conditions | Yield |
---|---|
In water at 55℃; | 92% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
phenyl isocyanate
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere; | 91% |
1,5-difluoro-2,4-dinitrobenzene
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
N-<2-<<<5-<(dimethylamino)methyl>-2-furanyl>methyl>thio>ethyl>-2,4-dinitro-5-fluoroaniline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile Ambient temperature; | 90% |
mefenamic Acid
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 15h; | 89% |
2-methylamino-2-methylthio-1-nitroethene
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
ranitidine
Conditions | Yield |
---|---|
In water at 55℃; | 88% |
In water at 38℃; under 75.0075 - 225.023 Torr; for 7h; | |
In water at 42℃; for 6h; Time; |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere; | 86% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
2-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With triethylamine In 1,2-dichloro-ethane at 20℃; for 3h; Inert atmosphere; | 85% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
2,4-Dinitrofluorobenzene
[2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-(2,4-dinitro-phenyl)-amine
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile Ambient temperature; | 84% |
2-chloro-4-isocyanato-1-methylbenzene
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
1-(3-chloro-4-methylphenyl)-3-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)urea
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 50℃; Inert atmosphere; | 81% |
1,5-difluoro-2,4-dinitrobenzene
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
N,N'-Bis-[2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-4,6-dinitro-benzene-1,3-diamine
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 3h; Heating; | 76% |
1,1-bis(benzylmercapto)-2-nitroethene
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
(1-benzylsulfanyl-2-nitro-vinyl)-(2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl)-amine
Conditions | Yield |
---|---|
In toluene at 100℃; for 3h; | 75% |
phthalic anhydride
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
2-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)isoindoline-1,3-dione
Conditions | Yield |
---|---|
In toluene for 2h; Reflux; Dean-Stark; | 72% |
1,8-Naphthalic anhydride
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
In toluene for 3h; Reflux; Dean-Stark; | 71.1% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
1,1-di(methylsulfanyl)-2-nitroethylene
1-<2-<(5-Dimethylaminomethyl-2-furyl)-methylthio>-ethylamino>-1-methylthio-2-nitroethylen
Conditions | Yield |
---|---|
In acetonitrile for 10h; Heating; | 69% |
In acetonitrile Heating; | |
In acetonitrile for 4h; Heating; | |
In acetonitrile at 90℃; for 8h; |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
6-Chloro-1H-benzoimidazole-2-sulfonic acid
(6-Chloro-1H-benzoimidazol-2-yl)-[2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-amine
Conditions | Yield |
---|---|
at 130℃; for 1.16667h; | 69% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
1,1-dioxo-1H-1λ6-[1,2,5]thiadiazole-3,4-diamine
A
4-<2-<5-(dimethylaminomethyl)furfurylthio>ethylamino>-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide
B
3,4-bis<2-<5-(dimethylaminomethyl)furfurylthio>ethylamino>-1,2,5-thiadiazole 1,1-dioxide
Conditions | Yield |
---|---|
With ammonium hydroxide for 12h; Ambient temperature; | A 69% B 70 mg |
1,4-difluoro-2-nitrobenzene
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
[2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-(4-fluoro-2-nitro-phenyl)-amine
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile Ambient temperature; | 68% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
4-amino-2-phenethyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide
A
4-[2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethylamino]-1,1-dioxo-2-phenethyl-1,2-dihydro-1λ6-[1,2,5]thiadiazol-3-one
B
C20H29N5O4S2
Conditions | Yield |
---|---|
In ethanol for 18h; Ambient temperature; | A 67% B 13% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
1,1-dioxo-1H-1λ6-[1,2,5]thiadiazole-3,4-diamine
3,4-bis<2-<5-(dimethylaminomethyl)furfurylthio>ethylamino>-1,2,5-thiadiazole 1,1-dioxide
Conditions | Yield |
---|---|
In water for 12h; Ambient temperature; | 67% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
4-amino-2-benzyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide
A
2-benzyl-4-<2-<5-(dimethylaminomethyl)furfurylthio>-ethylamino>-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1,-dioxide
B
2-amino-2-<(N-benzylsulphamoyl)imino>-N-<2-<5-(dimethylaminomethyl)furfurylthio>-ethyl>acetamide
Conditions | Yield |
---|---|
In ethanol for 18h; Ambient temperature; | A 66% B 24% |
In ethanol Ambient temperature; Yield given; |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
6-Methyl-1H-benzoimidazole-2-sulfonic acid
[2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-(6-methyl-1H-benzoimidazol-2-yl)-amine
Conditions | Yield |
---|---|
at 130℃; for 1.16667h; | 64% |
succinic acid anhydride
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
Conditions | Yield |
---|---|
With dmap In toluene for 3h; Reflux; Dean-Stark; | 63.6% |
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
2-methylsuccinic anhydride
Conditions | Yield |
---|---|
With dmap In toluene for 2h; Reflux; Dean-Stark; | 63.6% |
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