Dimethylformamide → 2-Furancarboxaldehyde, 5-(3,4-dimethoxyphenyl)-, O-[(methylamino)carbonyl]oxime

HRID 1759148Notes

Reaction equation

HRID 1759148 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:15][C:14]([CH:16]=[N:17][OH:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:19][N:20]([CH:22]=[O:23])C.CN=C=O>O>[CH3:19][NH:20][C:22]([O:18][N:17]=[CH:16][C:14]1[O:15][C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][CH:13]=1)=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12228Methyl IsocyanateHCID 71382179N-{[5-(3,4-Dimethoxyphenyl)furan-2-yl]methylidene}hydroxylamine

Product 1

HCID 540343162-Furancarboxaldehyde, 5-(3,4-dimethoxyphenyl)-, O-[(methylamino)carbonyl]oximeYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3,4-Dimethoxyphenyl)furylformaldoxime (9.5 g, 0.038 mole) and DMF (500 ml) was treated with methyl isocyanate (16 ml, 0.27 mole). The solution was stirred at room temperature for 4 hours and at steam bath temperature for 1 hour. The reaction solution was poured into 3 liters of water. The tan precipitate was collected to give 6 g (51%) of product.

Workup

  1. customThe tan precipitate was collected

Sources & evidence

ORD record
ord-82648de394dd45e3bbedeb24bc1918e0
Source dataset
uspto-grants-1982_07
Patent number
US04339386

Reaction notes

Loading…