Ethyl Acetate → 1-[4-(4-Chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride

HRID 463282Notes

Reaction equation

HRID 463282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([OH:17])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(OCC)(=O)C>N1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([O:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 109559944-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

Product 1

HCID 202825741-[4-(4-Chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]imidazole (20 g) in dry pyridine (100 ml) was cooled in an ice bath and treated dropwise with stirring with 7.0 ml of methanesulfonyl chloride. The mixture was allowed to come to room temperature overnight and diluted to 500 ml by the addition of ethyl acetate, with stirring. The resulting solid was then filtered off, washed with acetone and dried in air to give 1-[4-(4-chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride as a white solid (27.4 g).

Workup

  1. temperaturewas cooled in an ice bath
  2. additiontreated dropwise
  3. filtrationThe resulting solid was then filtered off
  4. washwashed with acetone
  5. customdried in air

Sources & evidence

ORD record
ord-5744abf3ba4f402596d1acbeec8a9e30
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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