Benzoyl chloride → HCID 86748035, compound

HRID 1741624Notes

Reaction equation

HRID 1741624 reaction equation
[CH:1]([C:4]1([CH3:30])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:19]=[CH:18][C:17]([CH2:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[N:5]1)([CH3:3])[CH3:2].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:31]([N:7]1[C:8](=[O:9])[C:4]([CH:1]([CH3:3])[CH3:2])([CH3:30])[N:5]=[C:6]1[C:10]1[N:19]=[CH:18][C:17]([CH2:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:22])=[O:23])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 86748036HCID 86748036, compound

Product 1

HCID 86748035HCID 86748035, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 5.9 g of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5 -[(phenylsulfonyl)methyl]nicotinic acid, methyl ester, and 0.3 g p-dimethylaminopyridine in 50 mL pyridine is stirred at room temperature and 1.75 mL benzoyl chloride is added in one portion. After stirring overnight, the reaction is concentrated in vacuo and the residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The aqueous phase is further extracted with methylene chloride, and the combined organic phases are dried and concentrated in vacuo. Chromatography of the residue on silica gel using hexane-ethyl acetate mixtures affords the desired product, mp 162°-166°.

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. customthe residue is partitioned between methylene chloride and aqueous sodium bicarbonate
  3. extractionThe aqueous phase is further extracted with methylene chloride
  4. customthe combined organic phases are dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e91d6b5122747b68fa873caf56034f9
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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