Hydrochloric Acid → HCID 54041926, compound

HRID 1414265Notes

Reaction equation

HRID 1414265 reaction equation
Cl.[CH2:2]([N:4]([CH2:37][CH3:38])[CH2:5][CH2:6][N:7]([S:33]([CH3:36])(=[O:35])=[O:34])[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:16][CH3:17])=[CH:10][CH:9]=1)[CH3:3].Cl>C(O)C>[CH2:37]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][N:7]([S:33]([CH3:36])(=[O:35])=[O:34])[C:8]1[CH:9]=[CH:10][C:11]([C:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:16][CH3:17])=[CH:12][CH:13]=1)[CH3:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21486678HCID 21486678, compound

Product 1

HCID 54041926HCID 54041926, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(2-Diethylaminoethyl)-4'-[1-hydroxy-2-(p-methoxyphenyl)-1-phenylbut-1-yl]methanesulfonanilide hydrochloride (34.5 g., 0.0616 mole) is dissolved in 200 ml. of concentrated hydrochloric acid and 200 ml. ethanol and the solution is refluxed for 1 hr. The ethanol is distilled under reduced pressure and the aqueous residue is basified with 50% aqueous NaOH to pH 11.0. The dehydration product is extracted with ethyl ether and the ether solution is washed with water, saturated sodium chloride, and dried (MgSO4). Distillation of the solvent yields 30.5 g. of an oil which is crystallized by dissolving in hot isopropanol and cooling the solution; 23.2 g., (75% yield with both Z and E isomers present in equal amounts), m.p. 120°-130°C.

Workup

  1. distillationThe ethanol is distilled under reduced pressure
  2. extractionThe dehydration product is extracted with ethyl ether
  3. washthe ether solution is washed with water, saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. distillationDistillation of the solvent
  6. customyields 30.5 g
  7. customof an oil which is crystallized
  8. dissolutionby dissolving in hot isopropanol
  9. temperaturecooling the solution

Sources & evidence

ORD record
ord-c38b91fa89274bfeb50d7457efdfc521
Source dataset
uspto-grants-1977_01
Patent number
US04001229

Reaction notes

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