N-bromobutanimide → 6-Bromomethyl-4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1295558Notes

Reaction equation

HRID 1295558 reaction equation
[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.[W]>[Br:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]2[O:8][CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 694178614-Methanesulfonyl-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 694200776-Bromomethyl-4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazineYield 100%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methanesulfonyl-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine (2.0 g, 8.8 mmol) and N-bromosuccinimide (1.88 g, 10.6 mmol) were dissolved in carbon tetrachloride (100 mL) and the mixture heated at reflux under a 250 W tungsten lamp. After 2 h the mixture was cooled to ambient temperature and filtered through Kieselguhr. The combined filtrate and washings were evaporated to dryness under reduced pressure to give the title compound (2.66 g, 100%) as a brown oil.

Workup

  1. temperaturethe mixture heated
  2. filtrationfiltered through Kieselguhr
  3. customThe combined filtrate and washings were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-71b8f1b2a2374a98aba49371a4cc6918
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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