تفاعل #58698

معادلة التفاعل

chloroacetonitrile

Acetonitrile

sodium bis(trimethylsilyl)amide

THF

Chloroacetonitrile

2-Chlorophenyl isothiocyanate

→

title compound

3-Amino-7-(2-chlorophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carbonitrile

المذيبات

EtOH

ظروف التفاعل

المعالجة

1. 1
   أخرىto give a thick white precipitate
2. 2
   أخرىto give a brown solution
3. 3
   درجة الحرارةthe mixture heated
4. 4
   درجة الحرارةat reflux for 24 h
5. 5
   أخرىVolatiles were removed in vacuo
6. 6
   workup.DISSOLUTIONthe residue dissolved in acetonitrile (100 mL)
7. 7
   درجة الحرارةthe mixture heated at 50° C. for 1 h
8. 8
   workup.ADDITIONwas added
9. 9
   درجة الحرارةheating
10. 10
    أخرىSome of the acetonitrile (˜50 mL) was removed in vacuo and water
11. 11
    workup.ADDITIONwas added
12. 12
    أخرىto precipitate the product
13. 13
    ترشيحThe brown solid was filtered off
14. 14
    غسيلwashed with water (50 mL) and Et2O (50 mL)
15. 15
    أخرىdried

الإجراء التجريبي

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)+.

المصدر