p-Fluoronitrobenzene → HCID 19992418, compound

HRID 345442Notes

Reaction equation

HRID 345442 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][NH:5][CH3:6].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:6][N:5]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[CH2:4][CH2:3][N:2]([CH3:1])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 516892Sodium BicarbonateHCID 19992421HCID 19992421, compound

Product 1

HCID 19992418HCID 19992418, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of part (i) (0.83 g), 4-fluoronitrobenzene (0.71 g) and sodium bicarbonate (1.0 g) in N,N-dimethylformamide (20 ml) was heated at 100° with stirring for 0.5 hour and then evaporated. The residue was stirred with water (2 ml) and the insoluble material was filtered off, washed with water and dried. The solid was chromatographed on silica gel. Elution with ethyl acetate/methanol (10:1) gave, after combination and evaporation of appropriate fractions, pure product (0.60 g), m.p. 126°-127° (from ethyl acetate/hexane).

Workup

  1. temperaturewas heated at 100°
  2. customevaporated
  3. stirringThe residue was stirred with water (2 ml)
  4. filtrationthe insoluble material was filtered off
  5. washwashed with water
  6. customdried
  7. customThe solid was chromatographed on silica gel
  8. washElution with ethyl acetate/methanol (10:1)
  9. customgave
  10. customafter combination and evaporation of appropriate fractions, pure product (0.60 g), m.p. 126°-127° (from ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d05de77dfeae4e1c82a1954d6f453b4b
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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