HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 2-[n-[4-(1,1-Dimethylethyl)benzoyl]amino]thiazole-5-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | 4-tert-Butylbenzoyl chloride | HCID 74372 | — |
| Reactant | 2-Amino-thiazole-5-carboxylic acid ethyl ester | HCID 314628 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[n-[4-(1,1-Dimethylethyl)benzoyl]amino]thiazole-5-carboxylic acid ethyl ester | HCID 20635344 | 88.2% |
Reaction Steps
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
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06956045B2 |
| Source dataset | uspto-grants-2005_10 |
| ORD ID | ord-c55b1bcf818248c68c0cbe5647fa4252 |
| Source note | uspto-grants-2005_10 |