p-Chlorothiophenol → 4-(4-Chlorophenylthio)-6-(4-methyl-1-piperazinyl)-2-phenylpyrimidine

HRID 1578979Notes

Reaction equation

HRID 1578979 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:2]2[CH:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]3)[N:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 7815p-ChlorothiophenolHCID 215573834-Chloro-6-(4-methyl-1-piperazinyl)-2-phenylpyrimidine

Product 1

HCID 215574144-(4-Chlorophenylthio)-6-(4-methyl-1-piperazinyl)-2-phenylpyrimidine

Conditions

Temperature
160 °C

Procedure

A well blended mixture of the above prepared 4-chloro-6-(4-methyl-1-piperazinyl)-2-phenylpyrimidine (2.0 g.) and 5.0 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. It amounted to 2.9 g. and melted at 145°-150°C. Upon recrystallization from absolute ethanol, there is obtained 4-(4-chlorophenylthio)-6-(4-methyl-1-piperazinyl)-2-phenylpyrimidine, m.p. 152°-154°C.

Workup

  1. additionmixture of the
  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 absolute ethanol

Sources & evidence

ORD record
ord-f89eb22c406b4b469b3ea1a5f684c937
Source dataset
uspto-grants-1976_02
Patent number
US03940395

Reaction notes

Loading…