3-Nitrobenzamide → HCID 19756852, compound

HRID 1588036Notes

Reaction equation

HRID 1588036 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15][CH:16]([N:18]=[C:19]=[O:20])[CH3:17]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][C:19]([NH:18][CH:16]([CH3:17])[CH3:15])=[O:20])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 125763-NitrobenzamideHCID 24758Sodium hydrideHCID 61277Isopropyl isocyanate

Product 1

HCID 19756852HCID 19756852, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-nitrophenylcarboxamide (2 g) in 25 ml of dry tetrahydrofuran was cooled to 0° C. and treated with 648 mg of sodium hydride (60% oil dispersion). The reaction mixture was stirred for 15 minutes and then 2-propylisocyanate (1.48 ml) was introduced dropwise via syringe. The reaction mixture was then stirred at 0° C. overnight. The reaction mixture was diluted with 300 ml of ethyl acetate. The reaction mixture was washed with 10% citric acid solution and brine. The organic extracts were dried and then concentrated in vacuo to yield 3.9 g of the title compound in sufficient purity to be used in the next step.

Workup

  1. stirringThe reaction mixture was then stirred at 0° C. overnight
  2. washThe reaction mixture was washed with 10% citric acid solution and brine
  3. customThe organic extracts were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4a3c561eb3f4f3795f15b44f275da02
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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