Acetanilide → HCID 10655068, compound

Temperature

80 °C

4-Chloro-1-(chloromethylthio)benzene (30 mmol) was added to a mixture of acetanilide (30 mmol) and potassium tert-butoxide (30 mmol) in DMF (75 ml). The mixture was stirred at 80° C. for 2 hours before the solvent was distilled off, the residue dissolved in chloroform and washed three times with water. The dried solution (MgSO4) was evaporated and the residue dissolved in ether. Remaining acetanilide was precipitated by adding Pet. ether and the solution evaporated. Yield 3.0 g. (43%). The crude product (13 mmol) was dissolved in CH2Cl2 (40 ml) and SO2Cl2 (13 mmol) in CH2Cl2 (10 ml) was added with stirring at 5° C. over 5 minutes. The mixture was stirred for 10 minutes before cyclohexene (14 mmol in CH2Cl2 (10 ml) was added. After stirring for 10 minutes at 5° C. the mixture was evaporated and the residue washed with Pet. ether and dried. Yield 0.70 g (29%). The product was used in Example 32 without purification. 1H NMR (CDCl3, δ): 1.92 (CH3), 5.50 (--SCH2), 7.1-7.7 (Ph).

1. distillationwas distilled off
2. dissolutionthe residue dissolved in chloroform
3. washwashed three times with water
4. customThe dried solution (MgSO4) was evaporated
5. dissolutionthe residue dissolved in ether
6. customRemaining acetanilide was precipitated
7. additionby adding Pet. ether
8. customthe solution evaporated
9. stirringwith stirring at 5° C. over 5 minutes
10. additionwas added
11. stirringAfter stirring for 10 minutes at 5° C. the mixture
12. customwas evaporated
13. washthe residue washed with Pet. ether
14. customdried
15. customThe product was used in Example 32 without purification

ORD record

ord-0bb6fea187fe498e9cab514ebdc775fd

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04705791