Dimethylformamide → HCID 86605783, compound

HRID 2221815Notes

Reaction equation

HRID 2221815 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:42])=[C:9]([CH2:11][O:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[C:25]4/[C:26](=[O:31])[NH:27][C:28](=[O:30])[S:29]/4)=[CH:22][N:21]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:20]=3)=[CH:15][C:14]=2[O:40][CH3:41])[N:10]=1.[CH3:43]N(C)C=O.[H-].[Na+].CI>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:42])=[C:9]([CH2:11][O:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[C:25]4/[C:26](=[O:31])[N:27]([CH3:43])[C:28](=[O:30])[S:29]/4)=[CH:22][N:21]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:20]=3)=[CH:15][C:14]=2[O:40][CH3:41])[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86605784HCID 86605784, compound

Product 1

HCID 86605783HCID 86605783, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (5Z)-5-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}methylene)-1,3-thiazolidine-2,4-dione (0.50 g) and N,N-dimethylformamide (10 mL) was added sodium hydride (60% in oil, 0.040 g) at room temperature. After stirring the reaction mixture at room temperature for 30 min, methyl iodide (0.16 g) was added, and the mixture was further stirred at room temperature for 30 hrs. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration to give (5Z)-5-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}methylene)-3-methyl-1,3-thiazolidine-2,4-dione as yellow crystals (0.47 g, yield 92%). Recrystallization from tetrahydrofuran-hexane gave yellow prism crystals. melting point: 215-216° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 hrs
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7cdecdfce1c3411b867ffe6fd3ebc756
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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