p-Chlorothiophenol → 4-[4-(4-Chlorophenylthio)-2-phenyl-6-pyrimidinyl]-1-piperazine ethanol

HRID 1578973Notes

Reaction equation

HRID 1578973 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][C:2]2[CH:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]3)[N:5]=[C:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7815p-ChlorothiophenolHCID 215573704-(4-Chloro-2-phenylpyrimidin-6-yl)-1-piperazineethanol

Product 1

HCID 867330864-[4-(4-Chlorophenylthio)-2-phenyl-6-pyrimidinyl]-1-piperazine ethanol

Conditions

Temperature
160 °C

Procedure

A well blended mixture of 3.8 g. of 4-(4-chloro-2-phenylpyrimidin-6-yl)-1-piperazineethanol and 7.0 g. of p-chlorothiophenol is heated in an oil bath maintaining the temperature at 160°C. for 3 hours. After being cooled to room temperature, the reaction mixture is triturated with 60 ml. of 30°/o sodium hydroxide. The product is collected on a sintered glass funnel and washed with water repeatedly. Upon recrystallization from 65°/o ethanol, there is obtained 4-[4-(4-chlorophenylthio)-2-phenyl-6-pyrimidinyl]-1-piperazine ethanol, m.p. 118°-120°C.

Workup

  1. additionmixture of 3.8 g
  2. temperatureAfter being cooled to room temperature
  3. customthe reaction mixture is triturated with 60 ml
  4. customof 30°
  5. customThe product is collected on a sintered glass funnel
  6. washwashed with water repeatedly
  7. customUpon recrystallization from 65°/o ethanol

Sources & evidence

ORD record
ord-932950528e324256943b3b0fbd3a3b67
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

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