Dimethylformamide dimethyl acetal → HCID 21484115, compound

HRID 1415290Notes

Reaction equation

HRID 1415290 reaction equation
[Cl:1][C:2]1[C:3](=[O:21])[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:5]=[CH:6][C:7]=1[N:8]([CH3:10])[NH2:9].[CH3:22]OC(OC)N(C)C>CN(C)C=O>[Cl:1][C:2]1[C:3](=[O:21])[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=2)[N:5]=[C:6]2[CH:22]=[N:9][N:8]([CH3:10])[C:7]=12

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 214841104-Chloro-5-(1-methylhydrazinyl)-2-[3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone

Product 1

HCID 21484115HCID 21484115, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml. of absolute dimethylformamide (dried over molecular sieves) under a nitrogen atmosphere, are dissolved 9.6 grams of 4-chloro-5-(1-methylhydrazino)-2-(3'-trifluoromethylphenyl)-3(2H)-pyridazinone. To this solution are added 3.9 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 3.9 grams of N,N-dimethylformamide dimethyl acetal are 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. 156°-158° 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-416663daf6db4e589aad241a50ff8979
Source dataset
uspto-grants-1977_01
Patent number
US04004009

Reaction notes

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