Isatoic Anhydride → N-(p-fluorobenzyl)isatoic anhydride

HRID 918192Notes

Reaction equation

HRID 918192 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].CC(N(C)C)=O.[H-].[Na+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:6]2[C:5](=[O:12])[O:4][C:2](=[O:3])[C:1]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:7]23)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8359Isatoic AnhydrideHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 31374Dimethylacetamide

Product 1

HCID 12223278N-(p-fluorobenzyl)isatoic anhydride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3.2 kgs. isatoic anhydride in 15 kgs. dimethylacetamide is added under nitrogen with stirring sodium hydride obtained from 880 gms. of a 57% dispersion in mineral oil, while maintaining the temperature below 25°C. The resulting mixture is heated to about 60°C. and held at about 55°-60°C. for 1 hour. The reaction mixture is then cooled to 20°-30°C. and to it is added 3.0 kgs. p-fluorobenzyl chloride. The mixture is then reheated to about 60°C. and held there for about 4 hours. It is then cooled again to 20°C. and to it is added 17.4 kgs. of ice and then 24 kgs. water. The mixture is stirred for 15 minutes, the solids collected by filtration, washed with several 2 kg. portions of water and then three times with 0.7 kg. diethylether. The washed solids are dried to obtain N-(p-fluorobenzyl)isatoic anhydride, m.p. 140°-143°C.

Workup

  1. customobtained from 880 gms
  2. temperatureof a 57% dispersion in mineral oil, while maintaining the temperature below 25°C
  3. temperatureThe reaction mixture is then cooled to 20°-30°C. and to it
  4. additionis added 3.0 kgs
  5. customis then reheated to about 60°C.
  6. waitheld there for about 4 hours
  7. temperatureIt is then cooled again to 20°C. and to it
  8. additionis added 17.4 kgs
  9. filtrationthe solids collected by filtration
  10. washwashed with several 2 kg
  11. customThe washed solids are dried

Sources & evidence

ORD record
ord-de241e202ab142e38d484ca9443ab576
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

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