Ethyl orthoformate → HCID 178468254, compound

HRID 1602276Notes

Reaction equation

HRID 1602276 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:3]=1[C:16]#[N:17].[CH2:18]([O:20][CH:21](OCC)OCC)[CH3:19]>C(O)C>[C:16]([C:3]1[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:5][NH:6][C:2]=1[N:1]=[CH:21][O:20][CH2:18][CH3:19])#[N:17]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 107280981H-Pyrazole-4-carbonitrile, 3-amino-5-[(3-methoxyphenyl)amino]-

Product 1

HCID 178468254HCID 178468254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

With stirring, a mixture of 4 g (17.45 mmol) of 5-amino-4-cyano-3-(3-methoxy-phenylamino)-pyrazole (Step 50.1) and 50 ml of orthoformic acid triethyl ester is heated at 120° C. for 1.5 hours, care being taken to ensure that the ethanol formed in the course of the reaction is distilled off from the reaction mixture. The reaction mixture is cooled to 30° C., approx. 100 ml of diethyl ether are added and the reaction mixture is cooled further to 0° C. and filtered. Washing with diethyl ether yields the title compound; m.p. 181-183° C.

Workup

  1. customformed in the course of the reaction
  2. distillationis distilled off from the reaction mixture
  3. temperatureThe reaction mixture is cooled to 30° C.
  4. additionapprox. 100 ml of diethyl ether are added
  5. temperaturethe reaction mixture is cooled further to 0° C.
  6. filtrationfiltered
  7. washWashing with diethyl ether

Sources & evidence

ORD record
ord-0da026190479461cafee09722ae91152
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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