Water → N-(p-fluorobenzyl)isatoic anhydride

HRID 970468Notes

Reaction equation

HRID 970468 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]Br)=[CH:18][CH:17]=1.O>CN(C)C=O>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=3[C:2](=[O:3])[O:4][C:5]2=[O:12])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 12223278N-(p-fluorobenzyl)isatoic anhydrideYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of isatoic anhydride (20 g, 122 mmol) in dimethylformamide (DMF) was added to a suspension of NaH (60% in mineral oil, 5.39 g, 135 mmol) in DMF and stirred at room temperature for 1 h. Then, 4-fluorobenzyl bromide (16.8 mL, 135 mmol) was added and the mixture stirred at room temperature for 4 h. The solution was poured into water and the solids formed were filtered, washed several times by water and dried. The solids were suspended in hexane, sonicated briefly, filtered, and washed by hexane to yield 30 g (90%) of white solids. M.P. 167° C. 1H NMR (DMSO-d6): δ 5.27 (s, 2H), 7.17 (t, J=8.8 Hz, 2H), 7.25 (d, J=8.4 Hz, 1H), 7.31 (t, J=7.4 Hz, 1H), 7.47 (m, 2H), 7.74 (t, J=7.0 Hz, 1H), 8.02 (d, J=7.8 Hz, 1H). Anal. (C15H10FNO3) C, H, N.

Workup

  1. stirringthe mixture stirred at room temperature for 4 h
  2. customthe solids formed
  3. filtrationwere filtered
  4. washwashed several times by water
  5. customdried
  6. customsonicated briefly
  7. filtrationfiltered
  8. washwashed by hexane

Sources & evidence

ORD record
ord-9c6d687a77cc4bf699279b6a373dab42
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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