Thiophosgene → HCID 13385585, compound

HRID 371363Notes

Reaction equation

HRID 371363 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][C:3]=1[NH2:4].[C:15](Cl)(Cl)=[S:16]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][C:3]=1[N:4]=[C:15]=[S:16]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 13519896Ethyl 5-amino-2,4-dichlorobenzoate

Product 1

HCID 13385585HCID 13385585, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

23.4 g (0.1 mol) of 2,4-dichloro-5-ethoxycarbonylaniline were dissolved in 80 ml of chloroform. The resulting solution was cooled to 10° C. or lower and 14.9 g (0.13 mol) of thiophosgene were added dropwise thereto. The mixture was stirred at room temperature for two hours, and then refluxed for three hours. The reaction mixture was concentrated to give 27 g (yield 97.7%) of the desired product as pale brown crystals with a melting point of 45°-46° C.

Workup

  1. temperaturerefluxed for three hours
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e4558d06794347dcaff55ae36aaec4a9
Source dataset
uspto-grants-1985_07
Patent number
US04531964

Reaction notes

Loading…