Dimethylformamide dimethyl acetal → HCID 21484113, compound

HRID 1415289Notes

Reaction equation

HRID 1415289 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([N:19]([CH3:21])[NH2:20])[CH:14]=[N:13]1.[CH3:22]OC(OC)N(C)C>CN(C)C=O>[CH3:21][N:19]1[C:15]2[C:14](=[N:13][N:12]([C:3]3[CH:4]=[C:5]([C:8]([F:11])([F:9])[F:10])[CH:6]=[CH:7][C:2]=3[F:1])[C:17](=[O:18])[CH:16]=2)[CH:22]=[N:20]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 21484112HCID 21484112, compound

Product 1

HCID 21484113HCID 21484113, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 250 ml. of absolute dimethylformamide (dried over molecular sieves) under a nitrogen atmosphere, are dissolved 14.5 grams of 2-(2-fluoro-5-trifluoromethylphenyl)-5-(1-methylhydrazino)-3(2H)-pyridazinone. To this solution are added 11.4 grams of N,N-dimethylformamide dimethyl acetal and the solution is heated at 110°-120° C. overnight. The progress of the reaction is followed by thin layer chromatography. An additional 6.0 grams of N,N-dimethylformamide dimethyl acetal is added with continued heating to complete the reaction (about 20 hours). The reaction mixture is then evaporated to dryness in vacuo and then column chromatographed on silica gel, eluting with a mixture of benzene-chloroform (50/50), to obtain the title product. (m.p. 190°-195° C.).

Workup

  1. temperaturethe solution is heated at 110°-120° C. overnight
  2. temperaturewith continued heating
  3. customthe reaction (about 20 hours)
  4. customThe reaction mixture is then evaporated to dryness in vacuo
  5. customcolumn chromatographed on silica gel
  6. washeluting with a mixture of benzene-chloroform (50/50)

Sources & evidence

ORD record
ord-d9543c7ff8224954a029389e01acb94a
Source dataset
uspto-grants-1977_01
Patent number
US04004009

Reaction notes

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