Acetyl chloride → HCID 14891477, compound

HRID 466357Notes

Reaction equation

HRID 466357 reaction equation
[CH2:1]([N:3]([CH2:11]N(CCCCCCC)CC)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2].C(Cl)(=O)C.[C:26]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[CH:31][CH:30]=1)(=[O:28])[CH3:27]>O1CCCC1>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][CH2:27][C:26]([C:29]1[CH:30]=[CH:31][C:32]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])=[CH:33][CH:34]=1)=[O:28])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 684083N-(4-acetylphenyl)methanesulfonamideHCID 14891475HCID 14891475, compound

Product 1

HCID 14891477HCID 14891477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Bis(ethylheptylamino)methane (0.95 g, 3.2 mmol) of Preparation 15 in 8 ml of tetrahydrofuran (THF), under nitrogen, is cooled in an ice bath and treated dropwise over 2 min with 0.23 ml (0.25 g, 3.2 mmol) of acetyl chloride; the mixture is stirred 15 min in the cold and 45 min at ambient temperature. The mixture is cooled in an ice bath and a solution of N-(4-acetylphenyl)methanesulfonamide, as described in Preparation 1, (dried by azeotrope from carbon tetrachloride then benzene) (0.68 g, 3.2 mmol) in 10 ml of THF is added dropwise over 5 min. It is stirred in the cold for 1 hr then at room temperature for 72 hrs. The solvent is removed in vacuo (bath <30° C.) and the residue partitioned between cold diluted HCl and ether. The layers are separated and the aqueous layer is extracted with additional ether (4×50 ml). The pooled ether extract is washed with cold diluted HCl. The aqueous layers are combined and brought to pH 8.5 with saturated NaHCO3. This is extracted with ethyl acetate (3×75 ml). The pooled ethyl acetate extract is washed with brine, dried (Na2SO4), acidified with excess ethereal HCl and concentrated to give a mixture which includes the title compound that can be used without further purification.

Workup

  1. temperatureunder nitrogen, is cooled in an ice bath
  2. temperatureThe mixture is cooled in an ice bath
  3. dry with material(dried by azeotrope from carbon tetrachloride
  4. additionbenzene) (0.68 g, 3.2 mmol) in 10 ml of THF is added dropwise over 5 min
  5. stirringIt is stirred in the cold for 1 hr
  6. waitat room temperature for 72 hrs
  7. customThe solvent is removed in vacuo (bath <30° C.)
  8. customthe residue partitioned between cold diluted HCl and ether
  9. customThe layers are separated
  10. extractionthe aqueous layer is extracted with additional ether (4×50 ml)
  11. extractionThe pooled ether extract
  12. washis washed with cold diluted HCl
  13. extractionThis is extracted with ethyl acetate (3×75 ml)
  14. extractionThe pooled ethyl acetate extract
  15. washis washed with brine
  16. dry with materialdried (Na2SO4)
  17. concentrationconcentrated
  18. customto give a mixture which

Sources & evidence

ORD record
ord-088316f0798c4878a2804e4050ad14c1
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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