Phosgene → 6-methyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].[O:11]1CCOC[CH2:12]1.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:10][C:4]1[S:3][C:2]2[NH:1][C:12](=[O:11])[O:8][C:7](=[O:9])[C:6]=2[CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
step 2—A suspension of 60b (4.0 g, 25.5 mmol) and dioxane (65 mL) was cooled to 5° C. Phosgene (22.5 mL of a 20% solution in toluene, 45.9 mmol) was added dropwise through a septum. The flask was equipped with a condenser and the mixture was refluxed for 4 h. After cooling the solvents were evaporated in vacuo to afford 5.0 g (100%) of 6-methyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione (61a) which was used without purification: ms [M−H]=182.
Workup
- customThe flask was equipped with a condenser
- temperaturethe mixture was refluxed for 4 h
- temperatureAfter cooling the solvents
- customwere evaporated in vacuo
Sources & evidence
- ORD record
- ord-83d333c553f744bfab35b5f66825a04e
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07479489B2
Reaction notes
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