Dimethyl Sulfate → 1-(4-methoxyphenyl)-4-{4-[3-(methylthio)4H-1,2,4-triazol-4-yl]phenyl}piperazine

HRID 1154732Notes

Reaction equation

HRID 1154732 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[N:24][N:23]=[C:22]4[SH:26])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].S(OC)(O[CH3:33])(=O)=O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[N:24][N:23]=[C:22]4[S:26][CH3:33])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 1784919634-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-4H-1,2,4-triazole-3-thiol

Product 1

HCID 128770271-(4-methoxyphenyl)-4-{4-[3-(methylthio)4H-1,2,4-triazol-4-yl]phenyl}piperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9 parts of 4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-4H-1,2,4-triazole-3-thiol, 2 parts of sodium hydroxide and 160 parts of methanol is stirred and warmed till all solid enters solution. Then there are added 3.3 parts of dimethyl sulfate and stirring is continued for 3 hours at room temperature. The reaction mixture is poured onto water. The precipitated product is filtered off and crystallized from 1-butanol, yielding 5.3 parts of 1-(4-methoxyphenyl)-4-{4-[3-(methylthio)-4H-1,2,4-triazol-4-yl]phenyl}piperazine; mp. 180° C.

Workup

  1. temperaturewarmed till all solid
  2. stirringstirring
  3. additionThe reaction mixture is poured onto water
  4. filtrationThe precipitated product is filtered off
  5. customcrystallized from 1-butanol

Sources & evidence

ORD record
ord-f653bfc0428c4bf8a9c2723a1349db39
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Reaction notes

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