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Synthetic route

3-chloro-2-methyl-quinolin-4-ol
31403-66-4, 83842-53-9

3-chloro-2-methyl-quinolin-4-ol

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Thiophosphoric acid O-(3-chloro-2-methyl-quinolin-4-yl) ester O',O''-diethyl ester
93516-24-6

Thiophosphoric acid O-(3-chloro-2-methyl-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
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
65673-93-0

3-Chlor-4-hydroxy-7-trifluormethylchinolin

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Thiophosphoric acid O-(3-chloro-7-trifluoromethyl-quinolin-4-yl) ester O',O''-diethyl ester
93516-26-8

Thiophosphoric acid O-(3-chloro-7-trifluoromethyl-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;A n/a
B 72%
4-hydroxy-2-methylquinoline
607-67-0

4-hydroxy-2-methylquinoline

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Quinothion
22439-40-3

Quinothion

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 70%
7-chloro-4-hydroxylquinoline
86-99-7

7-chloro-4-hydroxylquinoline

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Thiophosphoric acid O-(7-chloro-quinolin-4-yl) ester O',O''-diethyl ester
93516-22-4

Thiophosphoric acid O-(7-chloro-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 69%
4(1H)-quinolinone
529-37-3

4(1H)-quinolinone

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Thiophosphoric acid O,O'-diethyl ester O''-quinolin-4-yl ester
93516-19-9

Thiophosphoric acid O,O'-diethyl ester O''-quinolin-4-yl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 66%
7-trifluoromethyl-quinolin-4-ol
322-97-4

7-trifluoromethyl-quinolin-4-ol

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Thiophosphoric acid O,O'-diethyl ester O''-(7-trifluoromethyl-quinolin-4-yl) ester
93516-25-7

Thiophosphoric acid O,O'-diethyl ester O''-(7-trifluoromethyl-quinolin-4-yl) ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 65%
2,3-dimethylquinolin-4-ol
10352-60-0

2,3-dimethylquinolin-4-ol

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

Thiophosphoric acid O-(2,3-dimethyl-quinolin-4-yl) ester O',O''-diethyl ester
93644-61-2

Thiophosphoric acid O-(2,3-dimethyl-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;A n/a
B 63%
diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one
58861-80-6

4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one

A

sulfotep
3689-24-5

sulfotep

B

(5-Methyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
135492-37-4

(5-Methyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile a) 1 h, 35 deg C, b) 4 h, 50 deg C;A n/a
B 63%
diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

3,7-dichloroquinolin-4-ol
152210-26-9, 93516-30-4

3,7-dichloroquinolin-4-ol

A

sulfotep
3689-24-5

sulfotep

B

3,7-Dichloro-1-ethyl-1H-quinolin-4-one
93516-27-9

3,7-Dichloro-1-ethyl-1H-quinolin-4-one

C

Thiophosphoric acid O-(3,7-dichloro-quinolin-4-yl) ester O',O''-diethyl ester
93516-23-5

Thiophosphoric acid O-(3,7-dichloro-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
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
128070-22-4

5-benzyl-4,5-dihydro-1,2,4-triazin-6(1H)-one

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

(5-Benzyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
135492-46-5

(5-Benzyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;A n/a
B 53%
3-chloro-quinolin-4-ol
58550-89-3

3-chloro-quinolin-4-ol

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

3-chloro-1-ethyl-1H-quinolin-4-one
64965-21-5

3-chloro-1-ethyl-1H-quinolin-4-one

B

sulfotep
3689-24-5

sulfotep

C

Thiophosphoric acid O-(3-chloro-quinolin-4-yl) ester O',O''-diethyl ester
93516-21-3

Thiophosphoric acid O-(3-chloro-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
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
99822-19-2

5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

(5-Isopropyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
135492-43-2

(5-Isopropyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;A n/a
B 52%
diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

1,5-dimethyl-4,5-dihydro-1,2,4-triazine-6-one
135492-32-9

1,5-dimethyl-4,5-dihydro-1,2,4-triazine-6-one

A

sulfotep
3689-24-5

sulfotep

B

(1,5-Dimethyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
135492-38-5

(1,5-Dimethyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;A n/a
B 50%
1,3,4,5-tetrahydro<1,2,4>triazin 6(2H)-one
76990-32-4

1,3,4,5-tetrahydro<1,2,4>triazin 6(2H)-one

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

(6-Oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester
135492-34-1

(6-Oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
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
64965-46-4

3-methylquinolin-4-ol

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

1-(O,O-Diethylphosphorothio)-3-methyl-4-oxo-1,4-dihydroquinoline
93516-28-0

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
93516-20-2

Thiophosphoric acid O,O'-diethyl ester O''-(3-methyl-quinolin-4-yl) ester

Conditions
ConditionsYield
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
99822-19-2

5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one

O,O-dipropyl chlorothiophosphate
2524-05-2

O,O-dipropyl chlorothiophosphate

A

sulfotep
3689-24-5

sulfotep

B

[6-(Dipropoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-dipropyl ester
134202-30-5

[6-(Dipropoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-dipropyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;A n/a
B 28%
5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one
99822-19-2

5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

sulfotep
3689-24-5

sulfotep

B

[6-(Diethoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester
134202-29-2

[6-(Diethoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;A n/a
B 25%
diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one
58861-80-6

4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one

A

sulfotep
3689-24-5

sulfotep

B

[6-(Diethoxy-thiophosphoryloxy)-5-methyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester
134202-27-0

[6-(Diethoxy-thiophosphoryloxy)-5-methyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile 1.) 1 h, 35 deg C, 2.) 4 h, 50 deg C;A n/a
B 20%
pyridine
110-86-1

pyridine

Diethyl phosphate
598-02-7

Diethyl phosphate

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

Tetraethyl pyrophosphate
107-49-3

Tetraethyl pyrophosphate

B

tetraethyl thiopyrophosphate
645-78-3

tetraethyl thiopyrophosphate

C

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
das Natrium-Salz reagiert;
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
und Erhitzen des Reaktionsgemisches mit Schwefel;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With sulfuric acid
diphosphorous acid tetraethyl ester
21646-99-1

diphosphorous acid tetraethyl ester

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With sulfur at 160℃;
sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With Petroleum ether und anschliessenden Erwaermen mit Schwefel;
diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

O,O'-diethyl thiophosphoric acid
2465-65-8

O,O'-diethyl thiophosphoric acid

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With triethylamine
diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With pyridine; water
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With pyridine; sulfur; toluene
diphenylphosphinous acid methyl ester
4020-99-9

diphenylphosphinous acid methyl ester

bis(diethylphosphoryl)disulfide
4403-51-4

bis(diethylphosphoryl)disulfide

A

O,O-diethyl S-methyl phosphorothioate
2404-05-9

O,O-diethyl S-methyl phosphorothioate

B

sulfotep
3689-24-5

sulfotep

C

C16H20O4P2S

C16H20O4P2S

D

methyl diphenylphosphinate
1706-90-7

methyl diphenylphosphinate

Conditions
ConditionsYield
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Title compound not separated from byproducts;
tri-n-butyl phosphite
102-85-2

tri-n-butyl phosphite

bis(diethylphosphoryl)disulfide
4403-51-4

bis(diethylphosphoryl)disulfide

A

tetraethyl thiopyrophosphate
645-78-3

tetraethyl thiopyrophosphate

B

sulfotep
3689-24-5

sulfotep

C

diethyl S-tert-butyl thiophosphate
7795-74-6

diethyl S-tert-butyl thiophosphate

D

C12H28O6P2S

C12H28O6P2S

Conditions
ConditionsYield
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;
trineopentyl phosphite
14540-52-4

trineopentyl phosphite

bis(diethylphosphoryl)disulfide
4403-51-4

bis(diethylphosphoryl)disulfide

A

sulfotep
3689-24-5

sulfotep

B

C19H43O6P2S(1+)*C4H10O3PS(1-)

C19H43O6P2S(1+)*C4H10O3PS(1-)

C

C19H43O6P2S(1+)*C4H10O3PS(1-)

C19H43O6P2S(1+)*C4H10O3PS(1-)

Conditions
ConditionsYield
at -100 - -30℃; Mechanism;
bis(diethylphosphoryl)disulfide
4403-51-4

bis(diethylphosphoryl)disulfide

2-ethoxy-1,3,2-benzodioxaphosphole
10072-02-3

2-ethoxy-1,3,2-benzodioxaphosphole

A

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

B

tetraethyl thiopyrophosphate
645-78-3

tetraethyl thiopyrophosphate

C

sulfotep
3689-24-5

sulfotep

D

Thiophosphoric acid O,O'-diethyl ester O''-(2-oxo-2λ5-benzo[1,3,2]dioxaphosphol-2-yl) ester

Thiophosphoric acid O,O'-diethyl ester O''-(2-oxo-2λ5-benzo[1,3,2]dioxaphosphol-2-yl) ester

Conditions
ConditionsYield
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts;
sulfotep
3689-24-5

sulfotep

diethyl phosphorofluoridothioate
358-75-8

diethyl phosphorofluoridothioate

Conditions
ConditionsYield
With hydrogen fluoride

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