Triethylamine → 2-{[4-Cyano-2-methyl-3-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate

HRID 517732Notes

Reaction equation

HRID 517732 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])[C:3]=1[CH3:14].C(N(CC)CC)C.[C:22]([O:25][CH2:26][C:27](Cl)=[O:28])(=[O:24])[CH3:23]>ClCCl.O>[C:22]([O:25][CH2:26][C:27]([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])[C:3]=1[CH3:14])=[O:28])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 218752104-Amino-3-methyl-2-(trifluoromethyl)benzonitrile

Product 1

HCID 666550382-{[4-Cyano-2-methyl-3-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-3-methyl-2-(trifluoromethyl)benzonitrile (commercially available, for example from Sunshine Chemlab, Downington, Pa., USA, 500 mg, 2.50 mmol) and triethylamine (0.383 mL, 2.75 mmol) in dichloromethane (10 mL) was added 2-chloro-2-oxoethyl acetate (0.269 mL, 2.50 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM (100 ml) and water (50 ml) and aqueous was extracted with DCM (100 ml). The organics were combined, passed through a phase separator and concentrated to afford 710 mg of the title compound as a pale yellow powder.

Workup

  1. extractionaqueous was extracted with DCM (100 ml)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-45d0734b7d6a4fb383867eca26ffe178
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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