Acetonitrile → HCID 66970528, compound

Acetonitrile (10 mL) was added to a solution of sodium bis(trimethylsilyl)amide (100 mL, 1.0M in THF, 100 mmol) in THF (50 mL) at −78° C. to give a thick white precipitate. 2-Chlorophenyl isothiocyanate (7.72 g, 45.45 mmol) was added to give a brown solution. The mixture was allowed to warm to r.t. over 1 h then diluted with EtOH (50 mL). N,N-Dimethyluracil (6.4 g, 45 mmol) was added and the mixture heated at reflux for 24 h. Volatiles were removed in vacuo and the residue dissolved in acetonitrile (100 mL). Chloroacetonitrile (2.85 mL, 45 mmol) was added and the mixture heated at 50° C. for 1 h, a second charge of chloroacetonitrile (2.85 mL, 45 mmol) was added and heating continued for 1.5 h. Some of the acetonitrile (˜50 mL) was removed in vacuo and water was added to precipitate the product. The brown solid was filtered off, washed with water (50 mL) and Et2O (50 mL) and dried to give the title compound as a brown solid (14.3 g, quant.). δH (DMSO-d6) 8.10 (1H, d, J 9.7 Hz), 7.75-7.73 (1H, m), 7.65-7.54 (3H, m), 7.14 (2H, br s, NH2), 6.54 (1H, d, J 9.7 Hz). LCMS (ES+) RT 2.97 minutes, 302 (M+H)+.

1. customto give a thick white precipitate
2. customto give a brown solution
3. temperaturethe mixture heated
4. temperatureat reflux for 24 h
5. customVolatiles were removed in vacuo
6. dissolutionthe residue dissolved in acetonitrile (100 mL)
7. temperaturethe mixture heated at 50° C. for 1 h
8. additionwas added
9. temperatureheating
10. customSome of the acetonitrile (˜50 mL) was removed in vacuo and water
11. additionwas added
12. customto precipitate the product
13. filtrationThe brown solid was filtered off
14. washwashed with water (50 mL) and Et2O (50 mL)
15. customdried

ORD record

ord-70374f0cc4f742adabbac8ba060dc92f

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423047B2