Triethylamine → N-(5-bromothiazol-2-yl)-5-chloro-2-methoxybenzamide

HRID 254684

反応式

HRID 254684 の反応式
[NH2:1][C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21](Cl)=[O:22]>ClCCl.CN(C)C1C=CN=CC=1>[Br:7][C:4]1[S:3][C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:24]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[O:25][CH3:26])=[N:6][CH:5]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 436002-Thiazolamine, 5-bromo-HCID 123841765-Chloro-2-methoxybenzoyl chloride

生成物 1

HCID 60654877N-(5-bromothiazol-2-yl)-5-chloro-2-methoxybenzamide収率 66%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-amino-5-bromothiazole (1220 mg, 6.81 mmol) in dichloromethane (10 ml) was added triethylamine (1.235 ml, 8.86 mmol) and 4-dimethylamino pyridine (83 mg, 0.681 mmol), followed by addition of 5-chloro-2-methoxybenzoyl chloride (1397 mg, 6.81 mmol) and stirred overnight. The reaction was concentrated and water was added to the residue. The mixture was sonicated and filtered to obtain the title compound as off-white solid (1.56 g, 66%). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.88 (m, 3H) 7.23 (d, J=8.81 Hz, 1H) 7.58-7.67 (m, 3H) 12.32 (s, 1H); MS (DCI/NH3) m/z 347 (M+H)+.

後処理

  1. concentrationThe reaction was concentrated
  2. additionwater was added to the residue
  3. customThe mixture was sonicated
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-54016b6244354e10b3e7953c0f93d7db
出典データセット
uspto-grants-2011_01
特許番号
US07875640B2

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