Formanilide → HCID 11126692, compound

HRID 1982551Notes

Reaction equation

HRID 1982551 reaction equation
[Cl:1][C:2]1C=CC(SCCl)=CC=1.[CH:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].CC(C)([O-])C.[K+].C1CCCCC=1>CN(C=O)C.C(Cl)Cl>[Cl:1][CH2:2][N:13]([CH:11]=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7671FormanilideHCID 8079CyclohexeneHCID 23610Benzene, 1-chloro-4-((chloromethyl)thio)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 11126692HCID 11126692, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
80 °C

Procedure

4-Chloro-1-(chloromethylthio)benzene (21 mmol) was added to a mixture of formanilide (21 mmol) and potassium tert-butoxide (21 mmol) in DMF (200 ml). The mixture was stirred at 80° C. for 4 hours before the solvent was distilled off and the residue dissolved in ether and washed five times with water, and the dried (MgSO4) solution evaporated. Yield: 5.37 g (92%), m.p. 67° C. (Pet. ether/ether). The product (17.8 mmol) was dissolved in CH2Cl2 (100 ml) and SO2Cl2 (17.8 mmol) in CH2Cl2 (25 ml) was added with stirring at 5° C. for 30 minutes. The mixture was stirred for 15 minutes before cyclohexene (19.3 mmol) in CH2Cl2 (25 ml) was added. The mixture was evaporated and the residue washed with hexane and dried. The product was used in the Example 28 without further purification. 1H NMR (CDCl3,δ): 5.50 (s, --CH2 --), 7.34 (Ph), 8.33 (CHO).

Workup

  1. distillationwas distilled off
  2. dissolutionthe residue dissolved in ether
  3. washwashed five times with water
  4. dry with materialthe dried (MgSO4) solution
  5. customevaporated
  6. stirringwith stirring at 5° C. for 30 minutes
  7. additionwas added
  8. customThe mixture was evaporated
  9. washthe residue washed with hexane
  10. customdried
  11. customThe product was used in the Example 28 without further purification

Sources & evidence

ORD record
ord-69f63d556ca9446bb3160ea0e6ebdf5e
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

Loading…