Benzyl Bromide → HCID 22496209, compound

HRID 1015663Notes

Reaction equation

HRID 1015663 reaction equation
[C:1]1([C:7]2[S:15][C:14]3[C:13](=[O:16])[O:12][C:11](=[O:17])[NH:10][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(N(C)C)=O>[CH2:24]([N:10]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:15][C:14]=2[C:13](=[O:16])[O:12][C:11]1=[O:17])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 22496346HCID 22496346, compound

Product 1

HCID 22496209HCID 22496209, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 6-phenyl-1H-thieno[3,2-d][1,3]oxazine-2,4-dione (1 g, 4.1 mmol) and anhydrous sodium carbonate (477 mg, 4.5 mmol) diluted in 15 ml of anhydrous dimethylacetamide was stirred for one hour under nitrogen before adding benzyl bromide (785 mg, 4.5 mmol). The mixture was stirred overnight at room temperature. 912 mg (66.3%) of 1-benzyl-6-phenyl-1H-thieno[3,2-d][1,3]oxazine-2,4-dione were obtained as a pale yellow solid after filtration and washing the precipitate with acetone and pentane. NMR 1H (DMSO D6, 400 MHz) 7.8-7.76 ppm (m, 3H, Haro); 7.51-7.45 ppm (m, 3H, Haro); 7.43-7.41 ppm (m, 2H, Haro); 7.35-7.3 ppm (m, 2H, Haro); 7.28-7.24 ppm (m, 1H, Haro); 5.22 ppm (s, 1H, NCH2).

Workup

  1. stirringThe mixture was stirred overnight at room temperature

Sources & evidence

ORD record
ord-75e978d826714010b36aead6adeefd9c
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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