Hydrochloric Acid → 4-Formyl-N-[3-(trifluoromethoxy)phenyl]benzamide

HRID 1696612Notes

Reaction equation

HRID 1696612 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.[F:12][C:13]([F:23])([F:22])[O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].C1CCC(N=C=NC2CCCCC2)CC1.Cl>C(OCC)(=O)C>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:15]([O:14][C:13]([F:12])([F:22])[F:23])[CH:16]=2)=[O:3])=[CH:5][CH:6]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 120884-Formylbenzoic acidHCID 737533-(Trifluoromethoxy)aniline

Product 1

HCID 714239874-Formyl-N-[3-(trifluoromethoxy)phenyl]benzamideYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

to a solution of 300 mg of 4-carboxybenzaldehyde (2 mmoles) and 382 mg of 3-(trifluoromethoxy)aniline (2 mmoles) in 5 ml of ethyl acetate is added 830 mg of dicyclohexycarbodiimide (DCC) (4 mmoles). The reaction mixture is heated at 60° C. overnight and then poured into 60 ml of 1 N HCl solution. The mixture is extracted twice with 30 ml of ethyl acetate. The combined organic extracts are washed with 50 ml of water, 50 ml of a saturated solution of sodium bicarbonate and brine, dried over MgSO4 and concentrated. The crude product is purified on silica gel giving 233 mg of 4-Formyl-N-(3-trifluoromethoxy-phenyl)-benzamide (yield=38%). Analytical LC/MS method A: ([M+H]+): 310, RT: 5.60 min (gradient 5 to 85% acetonitrile in 7 min).

Workup

  1. extractionThe mixture is extracted twice with 30 ml of ethyl acetate
  2. washThe combined organic extracts are washed with 50 ml of water, 50 ml of a saturated solution of sodium bicarbonate and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6e63644f38c4a1bac475f821dcbfc85
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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