Acetic Acid → HCID 89760807, compound

HRID 1479162Notes

Reaction equation

HRID 1479162 reaction equation
CC([O-])(C)C.[K+].[CH3:7][C:8](NC(=O)C1C=CC=CC=1C(F)(F)F)([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[CH3:9].C(O)(=O)C.CCOC(C)=O>C1COCC1.CCOC(C)=O.C1CCCCC1.O>[C:8]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:20])([F:21])[F:19])([CH3:9])=[CH2:7]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 89760859HCID 89760859, compound

Product 1

HCID 89760807HCID 89760807, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of KOtBu in THF (1 M, 4.4 ml, 4.39 mmol) was added to a solution of N-[1-methyl-1-[[2-(trifluoromethyl)benzoyl]amino]ethyl]-2-(trifluoromethyl)benzamide (1.53 g, 3.66 mmol) in THF (10 ml). After 16 hours at room temperature the mixture was cooled to 0° C. and acetic acid (0.5 ml) added, and the mixture shaken between EtOAc and water, washed with NaHCO3 (1 M), brine, dried with MgSO4 and evaporated to yield 1.48 g of crude product which contained ca 20% starting material. Chromatography with EtOAc/cyclohexane yielded 451 mg (54%) N-isopropenyl-2-(trifluoromethyl)benzamide. M.p. 95-98° C.

Workup

  1. washwashed with NaHCO3 (1 M), brine
  2. dry with materialdried with MgSO4
  3. customevaporated
  4. customto yield 1.48 g of crude product which

Sources & evidence

ORD record
ord-852b128f6ebc43a8b202c8dc2c29f94e
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

Loading…