Ethanol → 5-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

HRID 49527Notes

Reaction equation

[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([CH:23]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)=[O:10])#[N:2].C([OH:28])C.OO.[OH-].[Na+]>O>[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([CH:23]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=1)=[O:10])(=[O:28])[NH2:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To 484 mg of 5-cyanomethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 10 ml of ethanol, 0.6 ml of 30% aqueous hydrogen peroxide and 5 ml of 0.1 mol/l sodium hydroxide, and the mixture was stirred for 1 hour at 50° C. Then, 0.6 ml of 30% aqueous hydrogen peroxide and 5 ml of 0.1 mol/l sodium hydroxide were added again and the mixture was stirred for 30 minutes at 50° C. The reaction mixture was poured into water and extracted with ethyl acetate. After washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence, the organic layer was dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel, methylene chloride:methanol=100:1 to 50:1) to obtain 318 mg of 5-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals.

Workup

stirringthe mixture was stirred for 30 minutes at 50° C
extractionextracted with ethyl acetate
washAfter washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence
dry with materialthe organic layer was dried over anhydrous sodium sulfate
distillationSolvent was distilled off under reduced pressure
customthe residue obtained
customwas purified by means of column chromatography (silica gel, methylene chloride:methanol=100:1 to 50:1)

Sources & evidence

ORD record: ord-35e359ae8a194026a6582d566ab31712
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706763B1

Reaction notes

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