Aniline → 4-Bromo-2-methoxy-N-phenylbenzamide

HRID 432257노트

반응식

HRID 432257 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](Cl)=[O:16])=[C:11]([O:18][CH3:19])[CH:10]=1.C(N(CC)CC)C>ClCCl>[C:2]1([NH:1][C:15](=[O:16])[C:12]2[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][C:11]=2[O:18][CH3:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6115AnilineHCID 8471TriethylamineHCID 223467824-Bromo-2-methoxybenzoyl chloride

생성물 1

HCID 223472094-Bromo-2-methoxy-N-phenylbenzamide수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Aniline(1.24 mL, 13.62 mmol) was added slowly to a mixture of 4-bromo-2-methoxy-1-benzenecarbonyl chloride (3.24 g, 12.98 mmol) and triethyl amine (2.7 mL, 19.48 mmol) in dichloromethane (130 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-phenyl-4-bromo-2-methoxybenzamide (2.92 g, 74%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 7.09 (s, 1H), 7.27 (m, 1H), 7.33 (m, 2H), 7.39 (s, 1H), 7.55 (d, J=8.15 Hz, 1H), 7.71 (m, 2H), 10.10 (s, 1H).

후처리

  1. customsolvent was removed under reduced pressure
  2. additionEthyl acetate was added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was re-crystallized from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-28951ed87c9d478a99cecefb1c23bf25
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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