Dimethylformamide → HCID 18944508, compound

HRID 1739569Notes

Reaction equation

HRID 1739569 reaction equation
[CH:1]([N:4]([CH:20]([CH3:22])[CH3:21])[C:5]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10](Cl)=[C:9]([N+:17]([O-:19])=[O:18])[CH:8]=1)=[O:6])([CH3:3])[CH3:2].CN(C)[CH:25]=[O:26]>[Cu]>[NH2:17][C:9]1[CH:8]=[C:7]([C:5]([N:4]([CH:1]([CH3:2])[CH3:3])[CH:20]([CH3:22])[CH3:21])=[O:6])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]=1[C:10]1[CH:11]=[CH:12][C:7]([C:5]([O:26][CH3:25])=[O:6])=[CH:8][CH:9]=1.[CH:1]([N:4]([CH:20]([CH3:22])[CH3:21])[C:5]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([C:10]2[CH:11]=[CH:12][C:7]([C:5]([O:26][CH3:25])=[O:6])=[CH:8][CH:9]=2)=[C:9]([N+:17]([O-:19])=[O:18])[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 21841484HCID 21841484, compound

Product 2

HCID 18944508HCID 18944508, compoundHCID 21841476HCID 21841476, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

1.67 g of the amide of Stage A, 1.39 g of methyl iodo benzoate (Preparation 7), 2.5 g of copper and 4 ml of dimethylformamide were mixed together in an autoclave at 200° C. for 90 minutes. After evaporation of the dimethyl-formamide, extraction was carried out with methylene chloride, followed by concentration under reduced pressure and purification by chromatography on silica, eluting with a cyclohexane/ethyl acetate mixture (7/3) to obtain 337.5 mg of Product A and 766 mg of Product B.

Workup

  1. customAfter evaporation of the dimethyl-formamide, extraction
  2. concentrationfollowed by concentration under reduced pressure and purification by chromatography on silica
  3. washeluting with a cyclohexane/ethyl acetate mixture (7/3)

Sources & evidence

ORD record
ord-8c73f25fa5bf4505b36d866d1270a799
Source dataset
uspto-grants-1999_10
Patent number
US05965763

Reaction notes

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