Dimethylformamide dimethyl acetal → HCID 58072342, compound

HRID 1624595Notes

Reaction equation

HRID 1624595 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([NH:9][N:10]=[C:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.[CH3:20]OC(OC)N(C)C>CN(C=O)C.Cl>[C:15]([C:11]1[C:12](=[O:14])[CH:13]=[CH:20][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:18])([F:19])[F:1])[CH:4]=2)[N:10]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178468329HCID 178468329, compound

Product 1

HCID 58072342HCID 58072342, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-{[3-(trifluoromethyl)phenyl]hydrazono}pentane-2,4-dione (5.00 g, 18.4 mmol) and N,N-dimethylformamide dimethyl acetal (2.44 mL, 18.4 mmol) in DMF (100 mL) was heated to 80° C. for 4 h. The mixture was diluted with 1 M HCl aqueous solution, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 80/20) and triturated with EtOAc/hexane to yield the title compound (3.38 g, 65% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 2.55 (3H, s), 6.75 (1H, d, J=8.0 Hz), 7.78-7.88 (2H, m), 8.06-8.16 (2H, m), 8.96 (1H, d, J=8.2 Hz).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 80/20)
  7. customtriturated with EtOAc/hexane

Sources & evidence

ORD record
ord-9c3db044aa024cf1a24ef2db1c3b2f15
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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