Bromine → HCID 58494903, compound

HRID 516258Notes

Reaction equation

HRID 516258 reaction equation
[CH2:1]([N:3]1[C:8]2=[CH:9][C:10]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12][C:11]=3[CH:24]=[C:7]2[O:6][CH2:5][CH2:4]1)[CH3:2].C(=O)([O-])O.[Na+].[Br:30]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClC(Cl)C>[Br:30][C:9]1[C:10]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12][C:11]=2[CH:24]=[C:7]2[O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:8]=12

Participants

6

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 58494639HCID 58494639, compound

Product 1

HCID 58494903HCID 58494903, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of 860 mg of t-butyl 4-ethyl-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate in 25 ml of dichloroethane was added 1.1 g of sodium hydrogen carbonate, and further, a solution of 200 μl of bromine in 5 ml of dichloroethane was added dropwise thereto over about 30 minutes, followed by stirring at room temperature. To the reaction mixture was slowly added a 3% aqueous sodium thiosulfate solution, followed by stirring vigorously and extracting with chloroform twice. The combined organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 490 mg of t-butyl 5-bromo-4-ethyl-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate.

Workup

  1. stirringby stirring vigorously
  2. extractionextracting with chloroform twice
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-c4685bcaf9224b67875698e75d3aa2f6
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

Loading…