Dimethylformamide diethylacetal → HCID 178489160, compound

HRID 1602246Notes

Reaction equation

HRID 1602246 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[C:3]=1[C:15]#[N:16].C(O[CH:20](OCC)[N:21]([CH3:23])[CH3:22])C>C1(C)C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:4]2[C:3]([C:15]#[N:16])=[C:2]([N:1]=[CH:20][N:21]([CH3:23])[CH3:22])[NH:6][N:5]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 178489159HCID 178489159, compound

Product 1

HCID 178489160HCID 178489160, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Under a N2 atmosphere, a suspension of 1.87 g (8.16 mmol) of 5-amino-3-(4-methoxy-phenyl)-1H-pyrazole-4-carbonitrile (for preparation see: J. Heterocyclic Chem. 27, 647 (1990)) in 33 ml of toluene is boiled under reflux for 3.5 hours with 1.64 ml of N,N-dimethylformamide diethyl acetal (95%; 9.1 mmol). Crystallization by cooling to 0° C., filtering with suction and washing with hexane yield N'-[3-(4-methoxy-phenyl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethylformamidine; m.p. 169-171° C.; TLC: Rf =0.18 (ethyl acetate:hexane=1:1); MS: (M)+ =269.

Workup

  1. customCrystallization
  2. filtrationfiltering with suction
  3. washwashing with hexane

Sources & evidence

ORD record
ord-dcc50de5404845e3a4d3d571130d2ab7
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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