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Triethylamine → 1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]-butane

HRID 844580
Notes
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Reaction equation

HRID 844580 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[C:19](=[O:28])[C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH3:36][S:37]([O:12][CH2:11][CH2:10][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19](=[O:28])[C:20]1[CH:21]=[C:22]([CH3:27])[CH:23]=[C:24]([CH3:26])[CH:25]=1)(=[O:39])=[O:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 226138373-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-ol

Product 1

HCID 226138261-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]-butaneYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

3-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-ol (0.63 g) (see Preparation 47) and triethylamine (0.20 g) were dissolved in dichloromethane (12 ml), cooled in an ice-bath and methanesulphonyl chloride (0.19 g) added. The mixture was stirred for 30 minutes, dichloromethane (35 ml) added and the solution washed sequentially with water (2×30 ml) and brine (30 ml). The organic phase was dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The residue was dissolved in acetonitrile and the solvent removed under reduced pressure to give 1-methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]-butane (0.72 g) as an oil.

Workup

  1. temperaturecooled in an ice-bath
  2. washthe solution washed sequentially with water (2×30 ml) and brine (30 ml)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in acetonitrile
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-338d198735dd4056adf5b9c2bb40d07f
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06380396B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes