Diisopropyl Ether → 4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-4H-1,2,4-triazole-3-thiol

HRID 2286544Notes

Reaction equation

HRID 2286544 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]([NH:21][C:22]([NH:24][NH2:25])=[S:23])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:26](O)(=O)C.C(=N)N.O(C(C)C)C(C)C>C(O)CCC>[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:26]=[N:25][N:24]=[C:22]4[SH:23])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 160693Formamidine acetateHCID 13368247N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]hydrazinecarbothioamide

Product 1

HCID 1784919634-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-4H-1,2,4-triazole-3-thiol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 23 parts of N-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}hydrazinecarbothioamide, 23 parts of methanimidamide acetate and 80 parts of 1-butanol is stirred and refluxed for 1 hour. The reaction mixture is cooled and poured onto water. 2,2'-oxybispropane is added. The precipitated product is filtered off, washed with water and with methanol and crystallized from 1-butanol, yielding 17.7 parts of 4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-4H-1,2,4-triazole-3-thiol; mp. 231.9° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water and with methanol
  6. customcrystallized from 1-butanol

Sources & evidence

ORD record
ord-43ebecb70d0a4db2a9e9ca72fb4c7759
Source dataset
uspto-grants-1981_05
Patent number
US04267179

Reaction notes

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