Sodium Iodide → HCID 68426247, compound

HRID 2261099Notes

Reaction equation

HRID 2261099 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12](Br)[CH:11](Br)[N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]=2[CH:23]=1)=[O:4].[Na+].[I-]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]=[CH:11][N:10]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:9]=2[CH:23]=1)=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 68427962HCID 68427962, compound

Product 1

HCID 68426247HCID 68426247, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3-Dibromo-2,3-dihydro-benzo[1,4]oxazine-4,6-dicarboxylic acid 4-tert-butyl ester 6-methyl ester (767 mg, 1.7 mmol) from proceeding step was stirred in acetone (14 ml) at RT for 2 h with NaI (1.27 g, 8.5 mmol). The solvent was removed, EtOAc, water and 1 M sodium thiosulfate were added. After separating phases the organic layer was washed with brine. The solvent was concentrated and the crude was purified on silica gel using CH/EtOAc 7:3 to obtain a colorless oil (456 mg, 92%).

Workup

  1. customThe solvent was removed
  2. additionEtOAc, water and 1 M sodium thiosulfate were added
  3. customAfter separating phases the organic layer
  4. washwas washed with brine
  5. concentrationThe solvent was concentrated
  6. customthe crude was purified on silica gel using CH/EtOAc 7:3

Sources & evidence

ORD record
ord-7f9c642268934822887b6cbcf87bbda5
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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