Hydrogen Bromide → methyl 2-bromo-3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-propionate

HRID 49534

반응식

HRID 49534 반응식
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]([O:33][CH3:34])(=[O:32])[CH:30]=[CH2:31]>CC(C)=O.CO>[Br:24][CH:30]([CH2:31][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:7](=[O:8])[NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:21]=1)[C:29]([O:33][CH3:34])=[O:32]

참가 물질

7

반응물 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 109034245-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamideHCID 23668193Sodium Nitrite

생성물 1

HCID 12094665methyl 2-bromo-3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-propionate

시약·촉매·용매 2

HCID 180Acetone용매HCID 887Methanol용매

반응 조건

온도
30 °C

실험 절차

To a solution of 17.3 g of 5-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide in 170 ml of acetone and 85 ml of methanol were added 43 ml of 47% solution of hydrobromic acid and 17 ml of aqueous solution of 4.15 g of sodium nitrite under cooling with ice-salt, and the mixture was stirred for 10 minutes. To the reaction mixture were added 26 ml of methyl acrylate, and, after heated to 30° C., 1.04 g of cupric oxide were added little by little, and the mixture was stirred further for 1 hour at 40 to 50° 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, and the residue obtained was crystallized from hexane-ethyl acetate, then the crystals were collected by filtration to obtain 10.3 g of methyl 2-bromo-3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-propionate as light brown crystals.

후처리

  1. stirringwas stirred further for 1 hour at 40 to 50° C
  2. distillationSolvent was distilled off under reduced pressure, and 25% aqueous ammonia
  3. additionwas added to the residue, which
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine in sequence
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationSolvent was distilled off under reduced pressure
  8. customthe residue obtained
  9. customwas crystallized from hexane-ethyl acetate
  10. filtrationthe crystals were collected by filtration

출처 및 근거

ORD 기록
ord-faaa6191dbe04481811664c513cd2e9a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706763B1

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