Potassium Carbonate → 1-[3-(4-Chlorobenzylthio)-2-(2,4-dichlorophenyl)-2-hydroxypropyl]-1,2,4-triazole

HRID 2164606Notes

Reaction equation

HRID 2164606 reaction equation
CS(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:16][O:15]1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][SH:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][S:29][CH2:16][C:14]([C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[Cl:6])([OH:15])[CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 804094-Chlorobenzyl mercaptanHCID 867396002-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane methanesulphonate

Product 1

HCID 204049251-[3-(4-Chlorobenzylthio)-2-(2,4-dichlorophenyl)-2-hydroxypropyl]-1,2,4-triazoleYield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane methanesulphonate salt (0.336 g, 1 mmole), 4-chlorobenzyl mercaptan, (0.159 g, 1 mmole) and anhydrous potassium carbonate (0.414 g, 3 mmole) were stirred in dry N,N-dimethylformamide (15 ml) at 70° C. for 72 hours. The reaction mixture was diluted with water (70 ml) and extracted with ethyl acetate (2×70 ml). The extracts were combined and evaporated to give an oil which crystallized on standing. Recrystallization from a mixture of ethyl acetate and n-hexane gave the title compound (0.23 g, 53%) m.p. 106°-107° C.

Workup

  1. extractionextracted with ethyl acetate (2×70 ml)
  2. customevaporated
  3. customto give an oil which
  4. customcrystallized
  5. customRecrystallization
  6. additionfrom a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-1e48621dde0b412b9d947daa316e2f21
Source dataset
uspto-grants-1985_03
Patent number
US04505919

Reaction notes

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