Pyridine → 2-[n-[4-(1,1-Dimethylethyl)benzoyl]amino]thiazole-5-carboxylic acid ethyl ester

HRID 966955

반응식

HRID 966955 반응식
[NH2:1][C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[C:12]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].N1C=CC=CC=1.CCCCCC>ClCCl>[CH2:10]([O:9][C:7]([C:4]1[S:3][C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:17][CH:18]=2)=[N:6][CH:5]=1)=[O:8])[CH3:11]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8058HexaneHCID 743724-tert-Butylbenzoyl chlorideHCID 3146282-Amino-thiazole-5-carboxylic acid ethyl ester

생성물 1

HCID 206353442-[n-[4-(1,1-Dimethylethyl)benzoyl]amino]thiazole-5-carboxylic acid ethyl ester수율 88.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of ethyl 2-aminothiazole-5-carboxylate (0.52 g, 3.0 mmol), 4-t-butylbenzoyl chloride (1.3 mL, 6.7 mmol) and pyridine (1.2 mL) in dichloromethane (10 mL) was stirred at 0° C. for 1.25 h. It was then diluted with dichloromethane and washed with aqueous HCl (1 N) twice, saturated aqueous sodium bicarbonate, and brine. After drying over sodium sulfate, filtration and concentration in vacuo gave a burgundy oil. Trituration with hexane afforded the desired amide as a light tan solid (0.88 g, 88% yield): LC/MS RT=3.85 min; mass spectrum (M+H)+=333.16. B. 4-(1,1-Dimethylethyl)-N-[(5-hydroxymethyl)thiazol-2-yl]benzamide

후처리

  1. washwashed with aqueous HCl (1 N) twice
  2. dry with materialAfter drying over sodium sulfate, filtration and concentration in vacuo
  3. customgave a burgundy oil

출처 및 근거

ORD 기록
ord-6ed2ac06f1a5428aab82304fcd0dfbe2
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953795B2

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