Chloroacetonitrile → HCID 86733425, compound

HRID 1076560Notes

Reaction equation

HRID 1076560 reaction equation
[Na].[CH2:2]([N:4]1[C:8]2=[N:9][C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]([C:13]([OH:15])=[O:14])[N:12]=[C:7]2[CH:6]=[N:5]1)[CH3:3].Cl[CH2:23][C:24]#[N:25]>CN(C)C=O>[CH2:2]([N:4]1[C:8]2=[N:9][C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]([C:13]([O:15][CH2:23][C:24]#[N:25])=[O:14])[N:12]=[C:7]2[CH:6]=[N:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 21537698HCID 21537698, compound

Product 1

HCID 86733425HCID 86733425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.8 g. of the sodium salt of 1-ethyl-6-phenyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid (0.02 mol.), 1.7 g. of chloroacetonitrile (0.22 mol.) and 70 ml. of dry dimethyl-formamide are heated in an autoclave at 120° for 5 hours. After vacuum removal of the solvent, the residual 1-ethyl-6-phenyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid, cyano-methyl ester is treated with water, filtered off, again treated with alcohol and then recrystallized from ethanol, yield 3.9 g. (64%), m.p. 102°-103°.

Workup

  1. customAfter vacuum removal of the solvent
  2. additionthe residual 1-ethyl-6-phenyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid, cyano-methyl ester is treated with water
  3. filtrationfiltered off
  4. additionagain treated with alcohol
  5. customrecrystallized from ethanol, yield 3.9 g

Sources & evidence

ORD record
ord-80ce6f73f2004ae390dfa5d2dfaa174e
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

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