Ethanol → HCID 10872742, compound

HRID 1004664Notes

Reaction equation

HRID 1004664 reaction equation
[Cl:1][C:2]1([C:5]([OH:21])([CH2:14][N:15]2[C:19]([SH:20])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1.[H-].[Na+].[C:24](Cl)(=[O:26])[CH3:25].C(O)C>O1CCCC1>[Cl:1][C:2]1([C:5]([OH:21])([CH2:14][N:15]2[C:19]([S:20][C:24](=[O:26])[CH3:25])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 178520209HCID 178520209, compound

Product 1

HCID 10872742HCID 10872742, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 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 in 20 ml of absolute tetrahydrofuran is admixed with stirring with 0.24 g (6 mmol) of sodium hydride (60% strength in paraffin oil) and stirred for 30 minutes. 0.72 ml (10 mmol) of acetyl chloride are then added and the reaction mixture is stirred at room temperature for a further 4 hours. The reaction mixture is then admixed with 1 ml of ethanol and concentrated under reduced pressure. The residue that remains is extracted repeatedly with dichloromethane. The combined organic phases are concentrated under reduced pressure. In this manner, 1.8 g (94% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-acetylmercapto-1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of an oil.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for a further 4 hours
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue that remains is extracted repeatedly with dichloromethane
  4. concentrationThe combined organic phases are concentrated under reduced pressure

Sources & evidence

ORD record
ord-bbe7c4542e254229bb6f8f97212cd3b6
Source dataset
uspto-grants-2000_04
Patent number
US06051592

Reaction notes

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