Water → 3-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate

HRID 844569Notes

Reaction equation

HRID 844569 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5](Cl)=[O:6].[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH2:21][CH2:22][OH:23])[CH:16]=[CH:17][C:18]=1[Cl:19].C(N([CH2:35][CH3:36])CC)C.[OH2:37]>C(#N)C.ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([O:23][CH2:22][CH2:21][CH:20]([C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=1)[CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:10](=[O:37])[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[C:35]([CH3:36])[CH:1]=1)=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 810883,5-Dimethylbenzoyl ChlorideHCID 226138293-(3,4-Dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol

Product 1

HCID 226138023-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3,5-Dimethylbenzoyl chloride (1.33 g) was added dropwise to a suspension of 3-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol (0.75 g) (see Preparation 19) and triethylamine (1.1 g) in anhydrous acetonitrile (15 ml) and the solution stirred at room temperature for 120 hours. The mixture was then mixed with water (30 ml) and dichloromethane (50 ml), the organic phase separated and washed sequentially with water and brine. The solvent was removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with a solvent gradient of 100:0 changing to 99:1, by volume, dichloromethane:methanol to give 3-(3,4-dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate (0.94 g) as a yellow foam.

Workup

  1. customthe organic phase separated
  2. washwashed sequentially with water and brine
  3. customThe solvent was removed under reduced pressure
  4. customto give a residue which
  5. customwas chromatographed on silica gel eluting with a solvent gradient of 100:0 changing to 99:1, by volume, dichloromethane

Sources & evidence

ORD record
ord-fb883548364c4ec7b8f18ae7517a2eec
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

Loading…