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

HRID 254684

반응식

HRID 254684 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-54016b6244354e10b3e7953c0f93d7db
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875640B2

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