Sodium hydride → HCID 21569038, compound

HRID 1579708Notes

Reaction equation

HRID 1579708 reaction equation
[H-].[Na+].[CH3:3][N:4]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[H][H].Br[CH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1>CN(C)C=O>[CH3:3][N:4]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[N:5]([CH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 255687Dibenzyl 1-methylhydrazine-1,2-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21569038HCID 21569038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension of 21.5 g. of sodium hydride in 80 ml. of dimethylformamide was added slowly, while stirring to a solution of 281 g. of 1-methyl-1,2-dicarbobenzoxy-hydrazine in 300 ml. of dimethylformamide. After the evolution of hydrogen had subsided, there was added to the reaction mixture a solution of 167 g. of 4-(bromomethyl)-benzonitrile in 200 ml. of dimethylformamide and the mixture was then heated for 1 hour at 80°. The solvent was then almost completely distilled off in vacuo, the residue triturated with water and extracted with ether. The ether extract was washed with water, dried and concentrated. By recrystallization from dibutylether, there was obtained the 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzonitrile melting at 68°.

Workup

  1. additionA suspension of 21.5 g
  2. additionthere was added to the reaction mixture a solution of 167 g
  3. distillationThe solvent was then almost completely distilled off in vacuo
  4. customthe residue triturated with water
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. customdried
  9. concentrationconcentrated
  10. customBy recrystallization from dibutylether

Sources & evidence

ORD record
ord-ce766ea9597a49f4b3bce8d60b9711dc
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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