Benzyl Bromide → HCID 86746476, compound

HRID 1646233Notes

Reaction equation

HRID 1646233 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+].[H][H].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([C:1]12[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]1[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 86746476HCID 86746476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
45 °C

Procedure

A solution of isatoic anhydride (4.1 gm) in DMF (30 ml) was added dropwise to a stirred suspension of 60% sodium hydride (1.0 gm) in DMF (20 ml) under nitrogen atmosphere. The reaction mixture was then warmed to 45° C. and stirred until hydrogen evolution ceased. The reaction mixture was then cooled and a solution of benzyl bromide (4.4 gm) in DMF (10 ml) was added slowly. Stirring was continued for one hour at room temperature and the solution was then evaporated under reduced pressure at 45° C. The resulting solid was suspended in methylene chloride, the insoluble inorganic solid was removed by filtration and the filtrate was evaporated to give 1-benzyl-isatoic anhydride.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customthe solution was then evaporated under reduced pressure at 45° C
  3. customthe insoluble inorganic solid was removed by filtration
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-54fea84faa8b41158ffc42510ba4d778
Source dataset
uspto-grants-1993_01
Patent number
US05179107

Reaction notes

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