Acetyl chloride → HCID 22063821, compound

HRID 1828206Notes

Reaction equation

HRID 1828206 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:13][NH:14][C:15]=3[CH3:16])=[CH:10][C:5]=2[N:4]([CH3:23])[C:3]1=[O:24].[CH2:25](N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[N:13][NH:14][C:15]=3[CH3:16])=[CH:10][C:5]=2[N:4]([CH3:23])[C:3]1=[O:24].[C:32]([N:14]1[C:15]([CH3:16])=[C:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3](=[O:24])[N:4]([CH3:23])[C:5]=3[CH:10]=2)[C:12]([C:17]2[CH:18]=[C:19]([CH3:25])[CH:20]=[CH:21][CH:22]=2)=[N:13]1)(=[O:34])[CH3:33]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22063821HCID 22063821, compound

Product 2

HCID 22063821HCID 22063821, compoundHCID 22063902HCID 22063902, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1,3-Dimethyl-5-(5-methyl-3-phenyl-1H-pyrazol-4-yl)-1,3-dihydro-benzoimidazol-2-one is prepared according to the procedures outlined in Example 337. 1,3-Dimethyl-5-(5-methyl-3-phenyl-1H-pyrazol-4-yl)-1,3-dihydro-benzoimidazol-2-one (70.9 mg) is diluted with dichloromethane and is treated with triethylamine (0.1 mL) and acetyl chloride (0.05 mL). The mixture is allowed to stir for 20 minutes then is diluted with saturated sodium bicarbonate and extracted into dichloromethane. The organic layer is dried over sodium sulfate and concentrated to give 8 mg 5-(1-Acetyl-5-methyl-3-m-tolyl-1H-pyrazol-4-yl)-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one.

Workup

  1. extractionextracted into dichloromethane
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bc7d072ac2164f8da0c7f4a87489eafc
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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