Sodium hydride → 3-(1-Methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile

HRID 349538Notes

Reaction equation

HRID 349538 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([CH:40]=O)[CH:17]=[N:16]1>O1CCCC1>[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([CH:40]=[CH:11][C:12]#[N:13])[CH:17]=[N:16]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 179619601-Methyl-5-triphenylmethylaminopyrazole-4-carbaldehyde

Product 1

HCID 693317453-(1-Methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrileYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (55% dispersion in mineral oil, 26.2 g, 600 mmol) in tetrahydrofuran (1000 ml) was added diethyl(cyanomethyl)phosphonate (106.3 g, 600 mmol) under ice-cooling. The mixture was stirred under ice-cooling for 20 minutes. To the mixture was added 1-methyl-5-triphenylmethylaminopyrazole-4-carbaldehyde (197 g, 530 mmol), and the mixture was stirred for 2 hours. The reaction mixture was poured into ice-cold water. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diethyl ether to give 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile (E, Z mixture, 126 g) as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. stirringthe mixture was stirred for 2 hours
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-efdb7497533745a4a77875ee3583e194
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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