Chloroacetonitrile → HCID 86733426, compound

HRID 1076563Notes

Reaction equation

HRID 1076563 reaction equation
[Na].[CH2:2]([N:4]1[C:8]2=[N:9][C:10]([CH3:16])=[C:11]([C:13]([OH:15])=[O:14])[N:12]=[C:7]2[CH:6]=[N:5]1)[CH3:3].Cl[CH2:18][C:19]#[N:20]>CN(C)C=O>[CH2:2]([N:4]1[C:8]2=[N:9][C:10]([CH3:16])=[C:11]([C:13]([O:15][CH2:18][C:19]#[N:20])=[O:14])[N:12]=[C:7]2[CH:6]=[N:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 21537672HCID 21537672, compound

Product 1

HCID 86733426HCID 86733426, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.12 g. of the sodium salt of 1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid (0.04 mol.), 3.33 g. of chloroacetonitrile (0.056 mol.) and 90 ml. of dimethyl-formamide are stirred at 70°-80° for 12 hours. After vacuum removal of the dimethylformamide, the residue is stirred with 200 ml. of ether and filtered. The ethereal filtrate is evaporated and the residual 1-ethyl-6-methyl-1H-pyrazolo[3,4-b]-pyrazine-5-carboxylic acid, cyanomethyl ester is recrystallized from hexane, yield 3.76 g. (38%), m.p. 83°-84°. A polymorphous form melts at 111°-112°.

Workup

  1. customAfter vacuum removal of the dimethylformamide
  2. filtrationof ether and filtered
  3. customThe ethereal filtrate is evaporated
  4. customthe residual 1-ethyl-6-methyl-1H-pyrazolo[3,4-b]-pyrazine-5-carboxylic acid, cyanomethyl ester is recrystallized from hexane, yield 3.76 g

Sources & evidence

ORD record
ord-e27b6f18c6cf42d09e176c9fe92591de
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

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