Dimethylformamide dimethyl acetal → HCID 20548490, compound

HRID 2058869Notes

Reaction equation

HRID 2058869 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](=[O:18])[CH2:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:7][CH:8]=1.CO[CH:23](OC)[N:24]([CH3:26])[CH3:25].Cl.CN>CO>[CH3:23][N:24]1[CH:26]=[C:11]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[C:10](=[O:18])[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:19])([F:20])[F:1])[CH:4]=2)=[CH:25]1

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 6364545Methylamine hydrochlorideHCID 20548491HCID 20548491, compound

Product 1

HCID 20548490HCID 20548490, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 6 g. portion of crude 1-(3-trifluoromethylphenyl)-2,4-octanedione was added 40 ml. of N,N-dimethylformamide dimethyl acetal and a few milliliters of methanol. The mixture was stirred under reflux overnight, and was then evaporated under vacuum to obtain 8.9 g. of a thick dark oil. The oil was taken up in 50 ml. of methanol, 9 g. of methylamine hydrochloride was added, and the mixture was stirred under reflux for 3 hours. It was then evaporated to a semi-solid under vacuum, and the residue was partitioned between diethyl ether and water. The organic layer was dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on a 300 g. silica gel column with 2:3 ethyl acetate:dichloromethane, and the product-containing fractions were combined and evaporated under vacuum to obtain 0.17 g. of the desired product in impure form. Nmr analysis in DMSOd6 showed peaks at δ7.6-8.3 (m, 6H, aromatic); 3.8 (s, 3H, N--CH3); 3.0-3.3 (t, 2H, COCH2); 0.7-1.8 (m, 7H, CH2CH2CH3).

Workup

  1. temperatureunder reflux overnight
  2. customwas then evaporated under vacuum
  3. customto obtain 8.9 g
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 3 hours
  6. customIt was then evaporated to a semi-solid under vacuum
  7. customthe residue was partitioned between diethyl ether and water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. customevaporated under vacuum
  10. customThe residue was chromatographed on a 300 g
  11. customevaporated under vacuum
  12. customto obtain 0.17 g

Sources & evidence

ORD record
ord-05783392b09f4819beb4690f9cc1aba2
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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