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

HRID 1004665Notes

Reaction equation

HRID 1004665 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1([C:15]([OH:31])([CH2:24][N:25]2[C:29]([SH:30])=[N:28][CH:27]=[N:26]2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:11][C:12]1([C:15]([OH:31])([CH2:24][N:25]2[C:29]([S:30][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:28][CH:27]=[N:26]2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 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 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature, a solution of 0.63 ml (5 mmol) of 4-chloro-benzoyl 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-61a411898c2c4502b50eb8ef1358da6b
Source dataset
uspto-grants-2000_04
Patent number
US06051592

Reaction notes

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