Dimethylformamide dimethyl acetal → (3E)-3-[(Dimethylamino)methylene]-1-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxocyclohexanecarbonitrile

HRID 2383980Notes

Reaction equation

HRID 2383980 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:23]#[N:24])[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)=[CH:5][CH:4]=1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>C1C=CC=CC=1>[CH3:27][N:28](/[CH:30]=[C:20]1\[CH2:21][C:16]([C:6]2[C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:23]#[N:24])[CH2:17][CH2:18][C:19]\1=[O:22])[CH3:29]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 248041271-(4-Methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile

Product 1

HCID 24804131(3E)-3-[(Dimethylamino)methylene]-1-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxocyclohexanecarbonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of the compound obtained in example 2 (200 mg, 0.626 mmol), dimethylformamide dimethylacetal (447 mg, 3.76 mmol) and a catalytic amount of tetraethyl amine in benzene (15 ml) were distilled over a period of 3 hrs to about one half the original volume. Benzene (15 ml) was added to the reaction mixture and the distillation was continued. The process was repeated until the reaction showed absence of the ketone starting material. After all starting material was consumed, the solvent was completely evaporated under vacuum and residue was purified by column chromatography to give 174 mg (74.5% yields) of an off-yellow solid product. Melting point (MP)-decomposes at 300° C.

Workup

  1. distillationthe distillation
  2. customAfter all starting material was consumed
  3. customthe solvent was completely evaporated under vacuum and residue
  4. customwas purified by column chromatography
  5. customto give
  6. custom174 mg (74.5% yields) of an off-yellow solid product
  7. customat 300° C.

Sources & evidence

ORD record
ord-a6a85a34034b437d9511d009f165fbcc
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

Loading…