Dimethylformamide dimethyl acetal → HCID 21484114, compound

HRID 1415291Notes

Reaction equation

HRID 1415291 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[N:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:6](=[O:20])[CH:5]=1)[NH2:3].[CH3:21]OC(OC)N(C)C>CN(C)C=O>[CH3:1][N:2]1[C:4]2[C:9](=[N:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=3)[C:6](=[O:20])[CH:5]=2)[CH:21]=[N:3]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 21484122HCID 21484122, compound

Product 1

HCID 21484114HCID 21484114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 225 ml. of absolute dimethylformamide (dried over molecular sieves) under a nitrogen atmosphere are dissolved 8.5 grams of 5-(1-methylhydrazino)-2-(3'-trifluoromethylphenyl)-3(2H)-pyridazinone. To this solution are added 7.1 grams of N,N-dimethylformamide dimethyl acetal and the solution is refluxed for 72 hours. The reaction is followed by thin layer chromatography The reaction mixture is then evaporated to dryness in vacuo and column chromatographed on silica gel, eluting with a mixture of benzene-chloroform (50/50), to obtain the crude title product which is then refined by preparative chromatography on a silica gel plate, eluting with chloroform to give crystalline title product, which is then washed with diethyl ether, m.p. 160°-163° C.

Workup

  1. temperaturethe solution is refluxed for 72 hours
  2. customis then evaporated to dryness in vacuo and column
  3. customchromatographed on silica gel
  4. washeluting with a mixture of benzene-chloroform (50/50)
  5. customto obtain the crude title product which
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-21b70bcfef2d4d3baa98375b19bb3894
Source dataset
uspto-grants-1977_01
Patent number
US04004009

Reaction notes

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