Water → HCID 19869519, compound

HRID 330400Notes

Reaction equation

HRID 330400 reaction equation
[Cl:1]CC[CH:4]([S:10][CH:11]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)CCCl)[C:5]1OC=CC=1.O.C(Cl)(Cl)Cl.[CH:25]([NH2:28])([CH3:27])[CH3:26]>>[ClH:1].[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[CH2:11][S:10][CH2:4][CH2:5][NH:28][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 6363IsopropylamineHCID 54347243HCID 54347243, compound

Product 1

HCID 19869519HCID 19869519, compound

Procedure

A solution of 2-chloroethyl-2-furanylmethyl sulfide in isopropylamine is agitated 8-12 hr in a stainless steel bomb at 80° C. The reaction mixture is then stripped to dryness and the residue is partitioned between water and chloroform. The chloroform layer is extracted with 1N sulfuric acid; whereupon two layers are obtained: a water phase (upper), and a chloroform phase (lower). The aqueous phase is made alkaline and extracted with chloroform. Evaporation of the organic layer yields the free base of the title compound, which is reacted with ethereal hydrogen chloride to give the hydrochloride salt which is then recrystallized from methanol/diethyl ether.

Workup

  1. customthe residue is partitioned between water and chloroform
  2. extractionThe chloroform layer is extracted with 1N sulfuric acid
  3. customwhereupon two layers are obtained
  4. extractionextracted with chloroform
  5. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-6d8b1f70f158445eb06e32243c1c9619
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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