Benzyl Bromide → 1-benzyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione

HRID 902522Notes

Reaction equation

HRID 902522 reaction equation
[H-].[Na+].[NH:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6](=[O:12])[O:5][C:4]1=[O:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([N:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6](=[O:12])[O:5][C:4]1=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 108775391H,2H,4H-thieno(2,3-d)(1,3)oxazine-2,4-dione

Product 1

HCID 110434681-benzyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dioneYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 1.0 g, 0.025 mol) was added to a solution of 1H-thieno[2,3-d][1,3]oxazine-2,4-dione (56) (3.53 g, 0.021 mol) in anhydrous DMF stirred at 0° C. under argon. The solution was stirred for 15 minutes before adding benzyl bromide (2.97 mL, 0.025 mol). The solution was allowed to come to room temperature and further stirred for 12 hours. The solution was poured into ice water and the precipitated solid was collected by vacuum filtration to yield 4.0 g (74%) of 1-benzyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione. 1H-NMR (DMSO-d6) δ 5.13 (s, 2H), 7.22 (d, J=5.6 Hz, 1H), 7.28 (d, J=5.6 Hz, 1H), 7.30-7.45 (m, 5H) ppm; EIMS m/z 260 (M+1).

Workup

  1. stirringThe solution was stirred for 15 minutes
  2. customto come to room temperature
  3. stirringfurther stirred for 12 hours
  4. filtrationthe precipitated solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-19ff1f9b4f6142b7b58256a24ca1d471
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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