Dimethylformamide diethylacetal → N'-(3-benzylamino-4-cyano-1H-pyrazol-5-yl)-N,N-dimethylformamidine

HRID 1068874Notes

Reaction equation

HRID 1068874 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=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>[CH2:8]([NH:7][C:4]1[C:3]([C:15]#[N:16])=[C:2]([N:1]=[CH:20][N:21]([CH3:23])[CH3:22])[NH:6][N:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 108224725-amino-3-benzylamino-1H-pyrazole-4-carbonitrile

Product 1

HCID 53832654N'-(3-benzylamino-4-cyano-1H-pyrazol-5-yl)-N,N-dimethylformamidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a suspension of 74.3 g (348 mmol) of 5-amino-3-benzylamino-1H-pyrazole-4-carbonitrile in 1.0 liter of toluene is boiled under reflux for 2 hours with 70.1 ml (95%; 409 mmol) of N,N-dimethylformamide diethyl acetal. Cooling to RT, filtration with suction and washing with diethyl ether yield N′-(3-benzylamino-4-cyano-1H-pyrazol-5-yl)-N,N-dimethyl-formamidine; m.p. 197-200° C.; TLC: Rf=0.50 (ethyl acetate).

Workup

  1. filtrationfiltration with suction
  2. washwashing with diethyl ether

Sources & evidence

ORD record
ord-b54cad5f2008443680dd410ed500e0f3
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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