Oxalyl chloride → 2-Fluorobenzoyl isocyanate
Reaction equation
[F: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>[F: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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
0.43 g (3.1 mmol) of 2-fluorobenzamide and 0.43 g (3.4 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-fluorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.85 g (3.1 mmol) of 2-bromo-4-chloro-5-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 0.82 g (Yield 60%) 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-d8785cc2bcea4d98974848d648d76598
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06051737
Reaction notes
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