Chloride → 2-(1-Chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(4-chloro-benzoyl-mercapto)-1,2,4-triazol-1-yl]-propan-2-ol

HRID 650643Notes

Reaction equation

HRID 650643 reaction equation
[Cl-:1].[Cl:2][C:3]1([C:6]([OH:22])([CH2:15][N:16]2[C:20]([SH:21])=[N:19][CH:18]=[N:17]2)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][CH2:4]1.[C:23](=[O:26])([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:2][C:3]1([C:6]([OH:22])([CH2:15][N:16]2[C:20]([S:21][C:23](=[O:26])[C:8]3[CH:13]=[CH:12][C:11]([Cl:1])=[CH:10][CH:9]=3)=[N:19][CH:18]=[N:17]2)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 312ChlorideHCID 11430Potassium CarbonateHCID 178520209HCID 178520209, compound

Product 1

HCID 179099552-(1-Chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(4-chloro-benzoyl-mercapto)-1,2,4-triazol-1-yl]-propan-2-olYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature, a solution of 0.63 ml (5 mmol) of 4-chloro-benzo)yl chloride in 5 ml of absolute tetrahydrofuran is added dropwise with stirring to a mixture of 1.72 g (5 mmol) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol, 0.69 g (5 mmol) of anhydrous potassium carbonate and 20 ml of absolute tetrahydrofuran. The reaction mixture is stirred at room temperature for a further 20 hours and then filtered off with suction and concentrated under reduced pressure. In this manner, 2.4 g (99% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(4-chloro-benzoyl-mercapto)-1,2,4-triazol-1-yl]-propan-2-ol are obtained in the form of an oil.

Workup

  1. filtrationfiltered off with suction
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f81a0c10d9b46469d73763270dea143
Source dataset
uspto-grants-2001_08
Patent number
US06274610B1

Reaction notes

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