Dimethylformamide dimethyl acetal → HCID 59436200, compound

HRID 1624641Notes

Reaction equation

HRID 1624641 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:24])[C:5](=[N:10][NH:11][C:12]1[C:22]([F:23])=[CH:21][C:15]2[O:16][C:17]([F:20])([F:19])[O:18][C:14]=2[CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:25]OC(OC)N(C)C>>[CH3:1][O:2][C:3]1[C:4](=[O:24])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[N:10][N:11]([C:12]2[C:22]([F:23])=[CH:21][C:15]3[O:16][C:17]([F:20])([F:19])[O:18][C:14]=3[CH:13]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496272HCID 178496272, compound

Product 1

HCID 59436200HCID 59436200, compoundYield 24%

Procedure

A mixture of methyl 4-methoxy-3-oxo-2-[(2,2,6-trifluoro-1,3-benzodioxol-5-yl)hydrazono]butanoate (6.31 g, 18.1 mmol) in N,N-dimethylformamide dimethyl acetal (63 mL) was heated to reflux for 2.5 h. The mixture was concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 70/30) and on basic silica gel (hexane/EtOAc=50/50 to 0/100) to yield the title compound (1.53 g, 24% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.79 (3H, s), 3.82 (3H, s), 7.94 (1H, d, J=9.4 Hz), 8.04 (1H, d, J=6.4 Hz), 8.54 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 70/30) and on basic silica gel (hexane/EtOAc=50/50 to 0/100)

Sources & evidence

ORD record
ord-208582dc43d1465d9005c8037342cb53
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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