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

HRID 432257ノート

反応式

HRID 432257 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 223472094-Bromo-2-methoxy-N-phenylbenzamide収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-28951ed87c9d478a99cecefb1c23bf25
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

反応ノート

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