Triethylamine → 2-{[4-Cyano-3-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C(N(CC)CC)C.[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>C(Cl)Cl>[C:21]([O:24][CH2:25][C:26]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:3]=1)=[O:27])(=[O:23])[CH3:22]Participants
Procedure
To a stirred solution of 4-amino-2-(trifluoromethyl)benzonitrile (commercially available, for example from Maybridge, Cornwall, United Kingdom, 85.0 g) in DCM (1 liter) at 0° C. was added triethylamine (92.2 g, 0.913 mol) and the reaction stirred for 15 minutes. Then acetoxyacetylchloride (74.5 g, 0.547 mol) was added at 0° C. and the reaction stirred for 4 hours at room temperature. The reaction mixture was diluted with DCM and washed with ice water followed by aqueous NaHCO3. The organic layer was separated and washed with brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by triturating with diethyl ether (500 mL) to yield 2-{[4-cyano-3-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate (85.0 g).
Workup
- customat 0° C.
- stirringthe reaction stirred for 4 hours at room temperature
- washwashed with ice water
- customThe organic layer was separated
- washwashed with brine solution
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude product was purified
- customby triturating with diethyl ether (500 mL)
Sources & evidence
- ORD record
- ord-c86d9a811d044dab94ac0ad2502089e1
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
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