Benzyl Bromide → HCID 18673278, compound

HRID 1058214Notes

Reaction equation

HRID 1058214 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:21]([N:7]1[C:6]2[CH:11]=[C:2]([Cl:1])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]=2[O:9][C:8]1=[O:10])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2415982(3h)-benzoxazolone, 5-chloro-6-nitro-2×

Product 1

HCID 18673278HCID 18673278, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

In a 250-ml flask, place 8.6 g (0.04 m) of 5-chloro-6-nitro-benzoxazol-2-one (2b, 1.3 g of tetrabutylammonium bromide, 11.1 g (0.08 m) of potassium carbonate powder, and 80 ml of acetone. Stir the mixture at 50° C. for 30 min. Add 7.4 g (0.04 m×1.08) of benzyl bromide. Stir the reaction mixture under reflux for 15 min. Distill off acetone, add 100 ml of water and 100 ml of toluene, stir for a few min. Separate toluene solution, wash with 100 ml of water, and concentrate under a reduced pressure to dryness to give 12.9 g (100%) of 3-N-benzyl-5-chloro-6-nitro-benzoxazol-2-one (4b; X=Cl) as a light brown oil.

Workup

  1. stirringStir the reaction mixture
  2. temperatureunder reflux for 15 min
  3. distillationDistill off acetone
  4. additionadd 100 ml of water and 100 ml of toluene
  5. stirringstir for a few min
  6. washSeparate toluene solution, wash with 100 ml of water
  7. concentrationconcentrate under a reduced pressure to dryness

Sources & evidence

ORD record
ord-b8c9d56d68b14440b02c4e2a76e6d626
Source dataset
uspto-grants-2003_02
Patent number
US06515176B1

Reaction notes

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