Water → HCID 22916731, compound

To a solution of 3.43 g (30 mmol) of 2-aminomethylthiazole and 3.34 g (33 mmol) of triethylamine in 60 ml of dichloromethane, a solution of 4.512 g of ethyl chloroxalate in 10 ml of dichloromethane was added dropwise with ice-cooling. The reaction solution was stirred for 30 minutes. 20 ml of water was added to the solution, and the mixture was stirred for 10 minutes. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (30 ml×5). The organic layers were combined, washed with a small amount of a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The resultant was concentrated to dryness under reduced pressure to give solid 2-(ethoxalylamino)methylthiazole. To this was added 50 ml of phosphorus oxychloride with ice-cooling. The mixture was refluxed for 12 hours, cooled to room temperature, and concentrated to dryness under reduced pressure. To the residue were added 50 ml of water and 50 ml of dichloromethane to obtain a solution. 50 g of potassium carbonate was added to the solution little by little with ice-cooling. The reaction solution was stirred for 10 minutes, and then filtered to remove insoluble matters. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (30 ml×2). The combined organic layers were dried over anhydrous potassium carbonate, and purified by flash column chromatography using silica gel, eluting with ethyl acetate to give 4.68 g (yield 80%) of the title compound as light yellow crystals.

1. temperaturecooling
2. stirringthe mixture was stirred for 10 minutes
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with dichloromethane (30 ml×5)
5. washwashed with a small amount of a saturated aqueous solution of sodium hydrogencarbonate
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationThe resultant was concentrated to dryness under reduced pressure

ORD record

ord-cac9b58c329a46bbb4068e0495e84d40

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05663162