Hydrogen Bromide → 5-(2-bromo-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

HRID 49530

Reaction equation

HRID 49530 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=[O:8].[BrH:24].N([O-])=O.[Na+].[C:29]([NH2:33])(=[O:32])[CH:30]=[CH2:31]>CC(C)=O.CO.O>[Br:24][CH:30]([C:29](=[O:32])[NH2:33])[CH2:31][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=1)=[O:8]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 6579AcrylamideHCID 109034245-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamideHCID 23668193Sodium Nitrite

Product 1

HCID 120946635-(2-bromo-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 2.26 g of 5-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide in 27 ml of acetone and 11 ml of methanol were added 5.6 ml of 47% solution of hydrobromic acid, 540 mg of sodium nitrite and 2 ml of water under cooling with ice, and the mixture was stirred for 10 minutes. To the reaction mixture were added 3.00 g of acrylamide, and, after heated to 30° C., 135 mg of cupric oxide were added little by little, and the mixture was stirred further for 2 hours at 30° C. Solvent was distilled off under reduced pressure, and 25% aqueous ammonia was added to the residue, which was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in sequence and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, the residue obtained was crystallized from hexane:ethyl acetate=1:1, and then the crystals were collected by filtration to obtain 1.55 g of 5-(2-bromo-2-carbamoylethyl)-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringwas stirred further for 2 hours at 30° C
  3. distillationSolvent was distilled off under reduced pressure, and 25% aqueous ammonia
  4. additionwas added to the residue, which
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine in sequence
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationSolvent was distilled off under reduced pressure
  9. customthe residue obtained
  10. customwas crystallized from hexane
  11. filtrationethyl acetate=1:1, and then the crystals were collected by filtration

Sources & evidence

ORD record
ord-166dbfddd38c4b35b4a216d8319fea93
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Linked notes

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