Thionyl Chloride → HCID 72272526, compound

HRID 641891Notes

Reaction equation

HRID 641891 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][NH:7][S:8]([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9])=O.O=S(Cl)[Cl:24]>>[Cl:24][C:4]([C:3]1[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=1[Cl:1])=[N:6][NH:7][S:8]([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 4249156HCID 4249156, compound2×

Product 1

HCID 72272526HCID 72272526, compound

Conditions

Temperature
75 °C

Procedure

Into a 500 mL round bottom flask was placed 2-chloro-N′-tosylbenzohydrazide (10 g, 30.79 mmol). To this was added SOCl2 (36.6 g, 307.56 mmol). The resulting solution was allowed to react, with stirring, for 1.5 hours while the temperature was maintained at 75° C. in a bath of oil. To the mixture was added 2-chloro-N′-tosylbenzohydrazide (10 g, 30.79 mmol), while cooling to a temperature of 60° C. The resulting solution was allowed to react, with stirring, for an additional 2 hours while the temperature was maintained at 75° C. in a bath of oil. The reaction mixture was then quenched by the adding 100 mL of n-hexane. A filtration was performed. The filter cake was washed with n-hexane. The solid was dried in an oven under reduced pressure. This resulted in 19.6 g (74%) of N′-(chloro(2-chlorophenyl)methylene)-4-methylbenzenesulfonohydrazide as a white solid.

Workup

  1. customInto a 500 mL round bottom flask was placed
  2. customto react
  3. temperaturewhile cooling to a temperature of 60° C
  4. customto react
  5. stirringwith stirring, for an additional 2 hours while the temperature
  6. temperaturewas maintained at 75° C. in a bath of oil
  7. customThe reaction mixture was then quenched by the adding 100 mL of n-hexane
  8. filtrationA filtration
  9. washThe filter cake was washed with n-hexane
  10. customThe solid was dried in an oven under reduced pressure
  11. customThis resulted in 19.6 g (74%) of N′-(chloro(2-chlorophenyl)methylene)-4-methylbenzenesulfonohydrazide as a white solid

Sources & evidence

ORD record
ord-4b1b851d6cf947fbb6626f1f9c393e01
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

Loading…