Diphosgene → 6-methylsulfanyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 893675Notes

Reaction equation

HRID 893675 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=O)[O:14]C(Cl)(Cl)Cl>O1CCOCC1>[CH3:12][S:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:13](=[O:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 127132522-Amino-5-(methylsulfanyl)benzoic acid

Product 1

HCID 127132556-methylsulfanyl-1H-benzo[d][1,3]oxazine-2,4-dioneYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of 9.16 parts of 2-amino-5-(methylthio)benzoic acid and 100 parts of 1,4-dioxane were added dropwise slowly 9.8 parts of trichloromethyl carbonochloridate. Upon completion, stirring was continued for 2 hours. The reaction mixture was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 8 parts (76%) of 6-(methylthio)-2H-3,1-benzoxazine-2,4(1H)-dione; mp. 219.4° C. (intermediate 153).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue was crystallized from acetonitrile
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-2c1fc213170848abac0b0e09fa3bede6
Source dataset
uspto-grants-1992_06
Patent number
US05126339

Reaction notes

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