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

HRID 576873Notes

Reaction equation

HRID 576873 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[OH-].[K+].ClC(Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>O.C1(C)C=CC=CC=1>[NH:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:8])[O:9][C:10]1=[O:16]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 94429Triphosgene

Product 1

HCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dioneYield 78.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-aminothiophene-2-carboxylate 20.0 g (0.127 mol) in water 150 ml was added the aqueous solution of potassium hydroxide 10.7 g (0.191 mol). The resulting solution wad heated to 90° C. for 2 hrs. After being checked by TLC till the starting material was consumed, the reaction solution was cooled to 0° C. Then a solution of triphosgene 18.9 g (0.064 mol) in toluene 150 ml was added dropwise. The resulting solution was stirred at room temperature for 2 hrs. The residue was filtered, and the solid was recrystallized from tetrahydrofuran to obtain 1H-thieno[3,2-d][1,3]oxazine-2,4-dione 8.5 g (yield 40%).

Workup

  1. customwas consumed
  2. temperaturethe reaction solution was cooled to 0° C
  3. filtrationThe residue was filtered
  4. customthe solid was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-863046949141439eb5804a3784e521f7
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

Loading…