Diphosgene → 1H,2H,4H-thieno(2,3-d)(1,3)oxazine-2,4-dione

HRID 902520Notes

Reaction equation

HRID 902520 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[OH-].[K+].ClC(OC(Cl)(Cl)Cl)=[O:15]>O>[NH:1]1[C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7](=[O:8])[O:9][C:10]1=[O:15]

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 14797Potassium HydroxideHCID 78381Methyl 2-amino-3-thenoate

Product 1

HCID 108775391H,2H,4H-thieno(2,3-d)(1,3)oxazine-2,4-dioneYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2-amino-thiophene-3-carboxylate (5 g, 31.72 mmol) was added to a solution of potassium hydroxide (3.55 g, 63.45 mmol) in 10 mL water. The solution was heated at 90° C. until to get a clear solution. The solution was then cooled to 0° C. and trichloromethyl chloroformate (5.74 mL, 47.57 mmol) was added slowly. The solution was allowed to come to room temperature and further stirred for 30 min. The precipitated solid was collected by vacuum filtration to yield 4.7 g (88%) of 1H-thieno[2,3-d][1,3]oxazine-2,4-dione. MP 233° C. 1H-NMR (DMSO-d6) δ 7.15 (d, J=6.0 Hz, 1H), 7.19 (d, J=6.0 Hz, 1H) ppm.

Workup

  1. customto get a clear solution
  2. temperatureThe solution was then cooled to 0° C.
  3. customto come to room temperature
  4. filtrationThe precipitated solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-2b08671b5da9486f9b882307b563774d
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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