Diisopropylethylamine → HCID 178429647, compound

Temperature

0 °C

To a solution of 3-methyl-thiophen-2-ylmethylamine (700 mg, 5.5 mmol) and Rhodanine (732 mg, 5.5 mmol) in acetonitrile (30 mL) was added DIPEA (1.91 mL, 11 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (1.52 g, 5.6 mmol) was added in one portion. After addition, the suspension was allowed to warm to room temperature and stirred for 3 days. The resulting black solids were filtered through a plug of celite and washed with acetonitrile (200 mL) and ethyl acetate (250 mL). The combined solvents were removed under the vacuum and the crude residue was dissolved in dichloromethane (150 mL) and washed with water (100 mL) and brine solution. After drying over anhydrous magnesium sulfate, the filtrate was removed under the vacuum and the residue was dissolved in dichloromethane (10 mL) and diluted with hexanes (10 mL). After cooling in the refrigerator overnight, the solids were collected by filtration and washed with dichloromethane. After drying in air, 390 mg (31.5% yield) of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one was isolated as a light yellow amorphous solid: EI-HRMS m/e calcd for C9H10N2OS2 (M+) 226.0235. found 226.0232.

1. additionAfter addition
2. temperatureto warm to room temperature
3. filtrationThe resulting black solids were filtered through a plug of celite
4. washwashed with acetonitrile (200 mL) and ethyl acetate (250 mL)
5. customThe combined solvents were removed under the vacuum
6. dissolutionthe crude residue was dissolved in dichloromethane (150 mL)
7. washwashed with water (100 mL) and brine solution
8. dry with materialAfter drying over anhydrous magnesium sulfate
9. customthe filtrate was removed under the vacuum
10. dissolutionthe residue was dissolved in dichloromethane (10 mL)
11. additiondiluted with hexanes (10 mL)
12. temperatureAfter cooling in the refrigerator overnight
13. filtrationthe solids were collected by filtration
14. washwashed with dichloromethane
15. customAfter drying in air

ORD record

ord-a2db05b295fc4c9fa2201c7da8d4b9f7

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07247727B2