Dimethyl Sulfoxide → 4-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-one

HRID 248133Notes

Reaction equation

HRID 248133 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.C(Cl)Cl.CS(C)=O.C(N(CC)CC)C>CCCCCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:17])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 109559944-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

Product 1

HCID 110103354-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-oneYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Alternatively, a mixture of 1-(4-(4-chlorophenyl)-2-hydroxybutyl)imidazole (1.8 kg, 7.18 mol), 2.25 equivalents of pyridine-sulfur trioxide complex and methylene chloride (8.6 L) stirred in the presence of excess dimethyl sulfoxide (19 L) and triethylamine (9 L) at 20°-35° C. for 3 hours. Upon completion of reaction, the mixture was combined with water (76 L) and hexane (34.4 L). The product was isolated, washed with water and hexane and dried to yield 4-(4-chlorophenyl)-1-(imidazol-1-yl)butan-2-one, 1.48 kg (83% yield).

Workup

  1. customUpon completion of reaction
  2. customThe product was isolated
  3. washwashed with water and hexane
  4. customdried

Sources & evidence

ORD record
ord-bd1d6f220c7e4bc5a1f0cdc24b47b2c8
Source dataset
uspto-grants-1993_05
Patent number
US05208331

Reaction notes

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