Water → N-(p-fluorobenzyl)isatoic anhydride

HRID 2170066Notes

Reaction equation

HRID 2170066 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[O:3][C:2]1=[O:12].[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:1]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4](=[O:11])[O:3][C:2]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 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 2H-3,1-benzoxazine-2,4(1H)-dione (1.0 g, 1.0 eq)) was taken up in N,N-dimethylformamide (15 ml) then treated with portion wise addition of sodium hydride (60% oil dispersion, 0.26 g, 1.05 eq). After stirring 30 minutes, p-fluorobenzyl bromide (1.22 g, 1.05 eq) was dripped in over 5 minutes. The reaction stirred at room temperature for 1 hour. A slurry of yellow solid resulted. Water (15 ml) was added to aid filtration. The solid was collected and recrystallized from ethyl acetate and hexanes (1:3) to afford 1.2 g (73%) of a brown crystalline solid. 1H-NMR (DMSO-d6): δ 8.0-7.9 (m, 1H), 7.8 (t, J=8.7 Hz, 1H), 7.5 (dd, J=8.7, 5.4 Hz, 2H), 7.3-7.0 (m, 4H), 5.3 (s, 2H); LC/MS calc M+Na 294, obs M+Na 294.

Workup

  1. customwas dripped in over 5 minutes
  2. stirringThe reaction stirred at room temperature for 1 hour
  3. customA slurry of yellow solid resulted
  4. customThe solid was collected
  5. customrecrystallized from ethyl acetate and hexanes (1:3)

Sources & evidence

ORD record
ord-12b178e81a5749ff8776bfc840bda077
Source dataset
uspto-grants-2015_06
Patent number
US09050334B2

Reaction notes

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