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

HRID 1533051
Notes
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Reaction equation

HRID 1533051 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent
HCID 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-b530072019eb47ecb39c936b778ecb21
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06207678B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes