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

HRID 843966Notes

Reaction equation

HRID 843966 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-71e870b6519b464ea7e6d31c3ec4b011
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

Loading…