Water → N-[2-[(4-Chlorophenyl)thio]ethyl]-1-methylethanamine hydrochloride

HRID 745154Notes

Reaction equation

HRID 745154 reaction equation
[Cl:1]CCC1C=C(Cl)C=[CH:6][C:5]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1CCCl.O.C(Cl)(Cl)Cl.[CH:27]([NH2:30])([CH3:29])[CH3:28]>>[ClH:1].[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([S:11][CH2:5][CH2:6][NH:30][CH:27]([CH3:29])[CH3:28])=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 6363IsopropylamineHCID 54258412Chloroethyl-p-chlorophenyl sulfide

Product 1

HCID 13655027N-[2-[(4-Chlorophenyl)thio]ethyl]-1-methylethanamine hydrochloride

Procedure

A solution of 24.0 g (0.116 mole) chloroethyl-p-chlorophenyl sulfide in 100 ml of isopropylamine was agitated overnight in a stainless steel bomb at 80° C. The reaction mixture was then stripped to dryness and the residue partitioned between water and chloroform. The chloroform layer was extracted with 1N sulfuric acid. Three layers were obtained: a water phase (lower), a chloroform phase (upper) and an intermediate phase. The aqueous and intermediate phases were combined, made alkaline and extracted with chloroform. Evaporation yielded an oil, the free base of the title compound. A portion of the oil was reacted with ethereal hydrogen chloride and the resulting hydrochloride salt was recrystallized from methanol-diethyl ether to give 2.23 g (22.6%) of white crystalline product, m.p. 126°-128° C.

Workup

  1. customthe residue partitioned between water and chloroform
  2. extractionThe chloroform layer was extracted with 1N sulfuric acid
  3. customThree layers were obtained
  4. extractionextracted with chloroform
  5. customEvaporation
  6. customyielded an oil

Sources & evidence

ORD record
ord-3d022173adda41db918c1913330fb835
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Reaction notes

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