Water → 4-fluoro-N-(4-nitrophenyl)benzamide

HRID 610665Notes

Reaction equation

HRID 610665 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.O>ClCCl>[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74754-NitroanilineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 39484284-fluoro-N-(4-nitrophenyl)benzamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 19.83 gm (143.56 mMol) 4-nitroaniline in 150 mL dichloromethane and 12.9 mL (159.5 mMol) pyridine at 0° C. were slowly added 24.5 gm (154.8 mMol) 4-fluorobenzoyl chloride. The reaction mixture was then stirred for 15 minutes at 0° C., at which time the reaction mixture became homogeneous, and then for an hour at room temperature. To this mixture were then added 100 mL water and the solid which formed was collected by filtration. The filter cake was washed with hexane (80 mL) followed by water (100 mL) and it was then dried under vacuum at 60° C. to give 34.1 gm (91%) N-(4-fluorobenzoyl)-4-nitroaniline.

Workup

  1. waitfor an hour at room temperature
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. washThe filter cake was washed with hexane (80 mL)
  5. customwas then dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-49d1773f28aa45eba7893c6c337666b1
Source dataset
uspto-grants-1999_12
Patent number
US05998630

Reaction notes

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