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Dimethylformamide → HCID 22227893, compound

HRID 1744563
Notes
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Reaction equation

HRID 1744563 reaction equation
[CH3:1]N(C)C=O.[C:6]([C:8]1[CH:9]=[C:10]([NH:20][C:21]([C:23]2[C:24]([CH3:35])=[N:25][N:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH:27]=2)=[O:22])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])#[N:7].[H-].[Na+].CI>O>[C:6]([C:8]1[CH:9]=[C:10]([N:20]([CH3:1])[C:21]([C:23]2[C:24]([CH3:35])=[N:25][N:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH:27]=2)=[O:22])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])#[N:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9909290N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)-3-methylpyrazole-4-carboxamide

Product 1

HCID 22227893HCID 22227893, compound

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To dimethylformamide (5 ml) solution containing N-(3-cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)-3-methylpyrazole-4-carboxamide (1.5 g) was added sodium hydride (60% content, 0.2 g) under ice-cooling and the mixture was stirred for 1 h. A solution of dimethylformamide (1 ml) containing methyl iodide (0.6 g) was added and the mixture was stirred under ice-cooling for 1 h. The mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: ethyl acetate:n-hexane=5:1) to give the title compound (0.5 g), melting point: 65–69° C.

Workup

  1. temperaturecooling
  2. additionwas added
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 1 h
  5. stirringstirred for 1 h
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (mobile phase: ethyl acetate:n-hexane=5:1)

Sources & evidence

ORD record
ord-20e4e001f5b2496b886f8e450f9dd4be
Source dataset
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07015218B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes