Dimethylcarbamoyl Chloride → 6-Dimethylcarbamoyl-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

HRID 2251603Notes

Reaction equation

HRID 2251603 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.[H-].[Li+].[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>>[CH3:28][N:29]([CH3:33])[C:30]([C:2]1[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1)=[O:31]

Participants

4

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 62714Lithium hydrideHCID 596429946-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

Product 1

HCID 596430226-Dimethylcarbamoyl-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

Procedure

6-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid (200 mg, 0.486 mmol), LiH (10 mg, 0.97 mmol, 2 eq.) and dimethylcarbamoylchloride (0.18 mL, 1.94 mmol, 4 eq.) as the electrophile were reacted according to GP4, Method B. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc/AcOH 67:30:3) to give the title compound as a colorless solid.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-efb204aca61948209e875fc1ac9fba27
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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