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

HRID 967734

Reaction equation

HRID 967734 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-c55b1bcf818248c68c0cbe5647fa4252
Source dataset
uspto-grants-2005_10
Patent number
US06956045B2

Linked notes

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