Dichloromethane → HCID 178418523, compound

HRID 3831Notes

Reaction equation

HRID 3831 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][SH:26])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(Cl)[Cl:28]>>[ClH:28].[ClH:28].[C:1]1([NH:7][C:8](=[SH:26][CH2:25][CH2:24][CH2:23][N:20]2[CH2:21][CH2:22][N:17]([C:14]3[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=3)[CH2:18][CH2:19]2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 7672Phenyl isocyanateHCID 13731131HCID 13731131, compound

Product 1

HCID 178418523HCID 178418523, compoundYield 33%

Procedure

1.2 g of phenyl isocyanate was added to a solution of 2.5 g of 3-[4-(4-fluorophenyl)piperazin-1-yl]propanethiol in 75 ml of methylene chloride, and the mixture was refluxed for four hours. After the further addition of 100 ml of methylene chloride the solution was washed with water, dried (sodium sulfate) and concentrated. The salt was precipitated with ethereal hydrochloric acid and recrystallized from aqueous ethanol to give 1.35 g (33% of theory) of N-phenyl-S-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}thiocarbamate dihydrochloride as a white crystalline solid, M.p. 250°-252° C.

Workup

  1. temperaturethe mixture was refluxed for four hours
  2. washwas washed with water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe salt was precipitated with ethereal hydrochloric acid
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-fb0f4206c10d4323b2412cb842391736
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Reaction notes

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