Oxalyl chloride → 2-Chlorobenzoyl isocyanate

HRID 1004871

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:12](Cl)=[O:13]>ClCCCl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:6]=[C:12]=[O:13])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

0.42 g (2.7 mmol) of 2-chlorobenzamide and 0.36 g (2.9 mmol, 1.1 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.7 g (2.7 mmol) of 2-bromo-4-fluoro-5-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 1.0 g (Yield 84%) of the title compound as a solid.

Workup

temperatureThe reaction solution was cooled down to room temperature
customThe reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-8bb7848e35aa40d5afa00537acbffed2
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051737

Linked notes

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