Water → 1-methyl-1H,2H,4H-thieno[3,2-d][1,3]oxazine-2,4-dione

HRID 557140Notes

Reaction equation

HRID 557140 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].[H-].[Na+].I[CH3:15].O>CN(C)C=O>[CH3:15][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]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

Product 1

HCID 136830851-methyl-1H,2H,4H-thieno[3,2-d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3.60 (21.3 mmol) 1H-Thieno(3,2-d)(1,3)oxazine-2,4-dione were dissolved in dried dimethylformamide and cooled to 0° C. 664 mg (27.7 mmol) sodium hydride was slowly added (Argon) and the mixture was stirred for 30 min at 0° C. and 30 min at room temperature. After cooling again to 0° C. 3.93 g (1.73 ml, 27.7 mmol) iodomethane were added. After stirring for 1 h at room temperature 200 ml water were added. The residue was filtrated and washed with water and ethyl ether.

Workup

  1. temperatureAfter cooling again to 0° C
  2. additionwere added
  3. filtrationThe residue was filtrated
  4. washwashed with water and ethyl ether

Sources & evidence

ORD record
ord-8e0904583b0e4493a38ac0660d2d6645
Source dataset
uspto-grants-2011_11
Patent number
US08058431B2

Reaction notes

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