3-chloro-2-methyl-quinolin-4-ol
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O-(3-chloro-2-methyl-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h; | A n/a B 74% |
3-Chlor-4-hydroxy-7-trifluormethylchinolin
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O-(3-chloro-7-trifluoromethyl-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h; | A n/a B 72% |
4-hydroxy-2-methylquinoline
diethyl phosphorochloridothioate
A
sulfotep
B
Quinothion
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h; | A n/a B 70% |
7-chloro-4-hydroxylquinoline
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O-(7-chloro-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h; | A n/a B 69% |
4(1H)-quinolinone
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O,O'-diethyl ester O''-quinolin-4-yl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h; | A n/a B 66% |
7-trifluoromethyl-quinolin-4-ol
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O,O'-diethyl ester O''-(7-trifluoromethyl-quinolin-4-yl) ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h; | A n/a B 65% |
2,3-dimethylquinolin-4-ol
diethyl phosphorochloridothioate
A
sulfotep
B
Thiophosphoric acid O-(2,3-dimethyl-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h; | A n/a B 63% |
diethyl phosphorochloridothioate
4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one
A
sulfotep
B
(5-Methyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile a) 1 h, 35 deg C, b) 4 h, 50 deg C; | A n/a B 63% |
diethyl phosphorochloridothioate
3,7-dichloroquinolin-4-ol
A
sulfotep
B
3,7-Dichloro-1-ethyl-1H-quinolin-4-one
C
Thiophosphoric acid O-(3,7-dichloro-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h; | A n/a B 16% C 62% |
5-benzyl-4,5-dihydro-1,2,4-triazin-6(1H)-one
diethyl phosphorochloridothioate
A
sulfotep
B
(5-Benzyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; | A n/a B 53% |
3-chloro-quinolin-4-ol
diethyl phosphorochloridothioate
A
3-chloro-1-ethyl-1H-quinolin-4-one
B
sulfotep
C
Thiophosphoric acid O-(3-chloro-quinolin-4-yl) ester O',O''-diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h; | A 17% B n/a C 52% |
5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one
diethyl phosphorochloridothioate
A
sulfotep
B
(5-Isopropyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; | A n/a B 52% |
diethyl phosphorochloridothioate
1,5-dimethyl-4,5-dihydro-1,2,4-triazine-6-one
A
sulfotep
B
(1,5-Dimethyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; | A n/a B 50% |
1,3,4,5-tetrahydro<1,2,4>triazin 6(2H)-one
diethyl phosphorochloridothioate
A
sulfotep
B
(6-Oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile 1.) 35 deg C, 1 h, 2.) 50 deg C, 4 h; | A n/a B 45% |
3-methylquinolin-4-ol
diethyl phosphorochloridothioate
A
sulfotep
B
1-(O,O-Diethylphosphorothio)-3-methyl-4-oxo-1,4-dihydroquinoline
C
Thiophosphoric acid O,O'-diethyl ester O''-(3-methyl-quinolin-4-yl) ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h; | A n/a B 21% C 31% |
5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one
O,O-dipropyl chlorothiophosphate
A
sulfotep
B
[6-(Dipropoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-dipropyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; | A n/a B 28% |
5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one
diethyl phosphorochloridothioate
A
sulfotep
B
[6-(Diethoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; | A n/a B 25% |
diethyl phosphorochloridothioate
4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one
A
sulfotep
B
[6-(Diethoxy-thiophosphoryloxy)-5-methyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile 1.) 1 h, 35 deg C, 2.) 4 h, 50 deg C; | A n/a B 20% |
pyridine
Diethyl phosphate
diethyl phosphorochloridothioate
A
Tetraethyl pyrophosphate
B
tetraethyl thiopyrophosphate
C
sulfotep
Conditions | Yield |
---|---|
das Natrium-Salz reagiert; |
diethyl phosphorylchloridite
sodium diethyl phosphite
sulfotep
Conditions | Yield |
---|---|
und Erhitzen des Reaktionsgemisches mit Schwefel; |
Conditions | Yield |
---|---|
With sulfuric acid |
diphosphorous acid tetraethyl ester
sulfotep
Conditions | Yield |
---|---|
With sulfur at 160℃; |
sodium diethyl phosphite
diethyl phosphorochloridothioate
sulfotep
Conditions | Yield |
---|---|
With Petroleum ether und anschliessenden Erwaermen mit Schwefel; |
diethyl phosphorochloridothioate
O,O'-diethyl thiophosphoric acid
sulfotep
Conditions | Yield |
---|---|
With triethylamine |
Conditions | Yield |
---|---|
With pyridine; water |
Conditions | Yield |
---|---|
With pyridine; sulfur; toluene |
diphenylphosphinous acid methyl ester
bis(diethylphosphoryl)disulfide
A
O,O-diethyl S-methyl phosphorothioate
B
sulfotep
D
methyl diphenylphosphinate
Conditions | Yield |
---|---|
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Title compound not separated from byproducts; |
tri-n-butyl phosphite
bis(diethylphosphoryl)disulfide
A
tetraethyl thiopyrophosphate
B
sulfotep
C
diethyl S-tert-butyl thiophosphate
Conditions | Yield |
---|---|
With trineopentyl phosphite In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts; | |
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
at -100 - -30℃; Mechanism; |
bis(diethylphosphoryl)disulfide
2-ethoxy-1,3,2-benzodioxaphosphole
A
O,O,S-triethyl phosphorothioate
B
tetraethyl thiopyrophosphate
C
sulfotep
Conditions | Yield |
---|---|
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With hydrogen fluoride |
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