Triethylamine → HCID 66654367, compound

HRID 517746Notes

Reaction equation

HRID 517746 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.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:3]=[C:4]([C:11]([F:12])([F:13])[F:14])[C:5]([C:6]#[N:7])=[CH:8][C:9]=1[CH3:10])=[O:28])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 66654425HCID 66654425, compound2×

Product 1

HCID 66654367HCID 66654367, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-5-methyl-2-(trifluoromethyl)benzonitrile (Intermediate 60, 300 mg, 1.50 mmol) and triethylamine (0.230 mL, 1.65 mmol) in dichloromethane (8 mL) was added 2-chloro-2-oxoethyl acetate (0.161 mL, 1.50 mmol) dropwise. The reaction mixture was stirred at room temperature overnight. Reaction mixture was diluted with DCM (100 ml) and water (50 ml) and aqueous was extracted with DCM (100 ml). Organics were combined, passed through a phase separator and concentrated to afford 452 mg of the title compound as a pale yellow powder.

Workup

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

Sources & evidence

ORD record
ord-1475515a26b14f96976a1360ec34d083
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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