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

HRID 918189Notes

Reaction equation

HRID 918189 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].[H-].[Na+].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CC(N(C)C)=O>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][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:18][CH:17]=1

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydride

Product 1

HCID 12223278N-(p-fluorobenzyl)isatoic anhydride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 16.3 g. of isatoic anhydride in 200 ml. of dimethylacetamide at room temperature is added sodium hydride obtained from 5.0 g. of 57% solution in mineral oil. The resulting mixture is stirred for 20 minutes and 16 g. of p-fluorobenzyl chloride is added followed by stirring at room temperature for about 15 hours. The resulting mixture is concentrated in vacuo to about one half its volume, a mixture of ice and water added and the resulting precipitate filtered off, washed with water, dried under suction and washed with pentane. The solid material is then dissolved in methylene chloride, dried with sodium sulfate, treated with charcoal and about twice the volume of diethyl ether added to crystallize N-(p-fluorobenzyl)isatoic anhydride, m.p. 142°-145°C.

Workup

  1. customobtained from 5.0 g
  2. stirringby stirring at room temperature for about 15 hours
  3. concentrationThe resulting mixture is concentrated in vacuo to about one half its volume
  4. additiona mixture of ice and water
  5. additionadded
  6. filtrationthe resulting precipitate filtered off
  7. washwashed with water
  8. customdried under suction
  9. washwashed with pentane
  10. dissolutionThe solid material is then dissolved in methylene chloride
  11. dry with materialdried with sodium sulfate
  12. additiontreated with charcoal
  13. additionabout twice the volume of diethyl ether added
  14. customto crystallize N-(p-fluorobenzyl)isatoic anhydride, m.p. 142°-145°C.

Sources & evidence

ORD record
ord-ea506e23f9834e66be498b7034bd33f9
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

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