Hydrochloric Acid → HCID 23345680, compound

HRID 1576223Notes

Reaction equation

HRID 1576223 reaction equation
BrC(C)C([C:5]1[CH:15]=[CH:14][C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][CH:6]=1)=O.C(#N)C.[ClH:20]>CC(=O)CC>[ClH:20].[CH3:13][S:10]([NH:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 13948301HCID 13948301, compound

Product 1

HCID 23345680HCID 23345680, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4'-(2-bromopropionyl)methanesulfonanilide (15.3 g., 0.05 mole) and α,60 -dimethylphenethylamine (16.42 g., 0.11 mole) in 200 ml. of acetonitrile is refluxed for a period of 16 hr. The product is isolated by concentrating the reaction mixture under reduced pressure, dissolving the residue in chloroform which is then washed with water, dried over magnesium sulfate, filtered through diatomaceous earth and concentrated to provide an oily residue of the crude product free base. The residue is taken up in butanone, acidified with ethanolic hydrogen chloride and the insoluble hydrochloride salt product collected, washed with butanone and dried. Crystallization of the hydrochloride salt from methanol-isopropyl alcohol and drying at high vacuum affords analytically pure 4'-[N-α,α-DIMETHYLPHENETHYL)-ALANYL]METHANESULFONANILIDE HYDROCHLORIDE, m.p. 236.0°-237.0°C. (dec.).

Workup

  1. customThe product is isolated
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. dissolutiondissolving the residue in chloroform which
  4. washis then washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through diatomaceous earth
  7. concentrationconcentrated
  8. customto provide an oily residue of the crude product free base
  9. customthe insoluble hydrochloride salt product collected
  10. washwashed with butanone
  11. customdried
  12. customCrystallization of the hydrochloride salt from methanol-isopropyl alcohol
  13. customdrying at high vacuum

Sources & evidence

ORD record
ord-024a98ebe04b4030ad3f7734b3d1628e
Source dataset
uspto-grants-1976_09
Patent number
US03979514

Reaction notes

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