Benzyl Bromide → HCID 11821306, compound

HRID 601140Notes

Reaction equation

HRID 601140 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])[O:3][C:2]1=[O:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:12]([N:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4](=[O:10])[O:3][C:2]1=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

Product 1

HCID 11821306HCID 11821306, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Example 110A (0.137 g, 0.81 mmol) was reacted with benzyl bromide (0.10 mL, 0.85 mmol), and potassium carbonate (0.134 g, 0.97 mmol) in dimethylformamide (5 mL) at ambient temperature for 20 hours. The reaction mixture was diluted with water and the resulting precipitate was collecte by filtration, and dried to give the title compound (0.165 g, 80%). MS (DCI/NH3) m/z 277 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 5.21 (s, 2 H) 7.25 (d, J=5.52 Hz, 1 H) 7.35 (m, 5 H) 8.28 (d, J=5.52 Hz, 1 H).

Workup

  1. filtrationthe resulting precipitate was collecte by filtration
  2. customdried

Sources & evidence

ORD record
ord-a4ffccd3fe5e47adbb73396b3cf19cbc
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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