Dimethylformamide → HCID 10279345, compound

HRID 1635578Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([N:14]([CH2:20][C:21]1[N:25]([CH3:26])[C:24]([CH3:27])=[CH:23][N:22]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13].[CH3:28][O:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1CCl.[CH3:38]N(C)C=O.[OH-].[K+]>O>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([N:14]([CH2:20][C:21]1[N:25]([CH2:26][C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[O:29][CH3:28])[C:24]([CH3:27])=[C:23]([CH3:38])[N:22]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 0.74 g (1.9 mmol) of (2-chloro-3,4-dimethoxyphenyl)-N-(3,4-dimethylimidazol-2-yl)methyl-N-(3-methylbutyl)carboxamide, 0.94 g (6.0 mmol) of 2-methoxybenzyl chloride, 10 mL of dimethylformamide and 0.63 mL (8.0 mmol) of 50% KOH is stirred vigorously under nitrogen at 40° C. for 20 h. The reaction mixture is poured into 100 mL of water and extracted with 50 mL of chloroform. The extract is washed with 100 mL of water, and the solvent is evaporated under reduced pressure. The residue is diluted with 50 mL of xylenes, and the volatiles are thoroughly evaporated under reduced pressure. Column chromatography of the residue on 30 g of silica gel using chloroform-diethyl ether (98:2, v/v) as an eluent afforded 646 mg (67%) of the title compound as a cream colored foam. Mass Spec m/z (M++1) 514.

Workup

extractionextracted with 50 mL of chloroform
washThe extract is washed with 100 mL of water
customthe solvent is evaporated under reduced pressure
additionThe residue is diluted with 50 mL of xylenes
customthe volatiles are thoroughly evaporated under reduced pressure

Sources & evidence

ORD record: ord-af498c13bfdc4d3cbb77754fe8f9cdee
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509366B2

Reaction notes

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