Chloroacetyl chloride → 2-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:17])=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:17])=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=1)=[O:4]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a round bottom flask was added chloroacetyl chloride (2.0 mL, 25.0 mmol, 1.0 eq.) and CH2Cl2 (100 mL). The solution was cooled to 0° C. before a mixture of 5-amino-2-chloro-benzotrifluoride (4.88 g, 25.0 mmol, 1.0 eq.) and triethyl amine (3.56 mL, 27.5 mmol, 1.1 eq.) in CH2Cl2 (5.0 mL) was added dropwise. The reaction was then stirred at 0° C. for 1.5 h before quenching with H2O (50 mL). The organic layer was then separated, washed with brine, and dried with Na2SO4. Concentration via rotary evaporation gave acetamide 21 as a yellow solid (5.72 g, 84.7% yield). 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.79 (br s, 1H), 8.20 (d, 1H), 7.87 (dd, 1H), 7.75 (d, 1H), 4.36 (s, 2H) ppm.
Workup
- additionwas added dropwise
- custombefore quenching with H2O (50 mL)
- customThe organic layer was then separated
- washwashed with brine
- dry with materialdried with Na2SO4
- concentrationConcentration
- customvia rotary evaporation
Sources & evidence
- ORD record
- ord-827dbbb3ee154d9e9d1c7e5a8ea9fd62
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362017B2
Reaction notes
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