Thionyl Chloride → 3-(Chloroacetylamino)benzoylchloride

HRID 839042Notes

Reaction equation

HRID 839042 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=[O:14])=[O:8]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([Cl:3])=[O:14])=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21698603-(2-Chloroacetamido)benzoic acid

Product 1

HCID 227543773-(Chloroacetylamino)benzoylchlorideYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a warm (55°-60° C.) solution of 250 ml. of thionyl chloride and 50 ml. of chloroform and 6 drops of pyridine is added 3-(chloroacetylamino)benzoic acid (150 g., 0.702 mole) in 3 equal portions at 0.5 hr. intervals. After the addition is complete, the reaction mixture is warmed to a temperature of 55°-65° C. for 2 hrs., cooled and diluted with 500 ml. of petroleum ether (b.p. 30°-60° C.). The precipitate which forms is collected, washed with petroleum ether (b.p. 30°-60° C.) and dried under vacuum over potassium hydroxide at room temperature to afford 143 g. (80% yield) of 3-(chloroacetylamino)benzoyl chloride, m.p. 106°-108° C.

Workup

  1. temperatureTo a warm (55°-60° C.) solution of 250 ml
  2. additionAfter the addition
  3. temperaturethe reaction mixture is warmed to a temperature of 55°-65° C. for 2 hrs
  4. temperature, cooled
  5. additiondiluted with 500 ml
  6. customThe precipitate which forms is collected
  7. washwashed with petroleum ether (b.p. 30°-60° C.)
  8. dry with materialdried under vacuum over potassium hydroxide at room temperature
  9. customto afford 143 g

Sources & evidence

ORD record
ord-ddfd3580717743deb6d10d3cf600047c
Source dataset
uspto-grants-1978_06
Patent number
US04093739

Reaction notes

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