Phosgene → 3-Methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonylisocyanate

HRID 280447Notes

Reaction equation

HRID 280447 reaction equation
[CH3:1][C:2]1[S:3](=[O:21])(=[O:20])[O:4][C:5]2[C:11]([S:12]([NH:15][C:16](NC)=[O:17])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1.C(Cl)(Cl)=O>ClC1C=CC=CC=1>[CH3:1][C:2]1[S:3](=[O:21])(=[O:20])[O:4][C:5]2[C:11]([S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20195199N-(3-Methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea

Product 1

HCID 201952003-Methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonylisocyanate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

5.0 g of N-(3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea are dispersed in 150 ml of absolute chlorobenzene and the dispersion is saturated with phosgene at 130° C. A clear solution forms during this addition. The solvent is subsequently distilled off in vacuo with the exclusion of moisture. The 3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonylisocyanate obtained as oily residue can be used without further purification for the preparation of the pyrimidinylureas and triazinylureas of the formula I.

Workup

  1. additionA clear solution forms during this addition
  2. distillationThe solvent is subsequently distilled off in vacuo with the exclusion of moisture

Sources & evidence

ORD record
ord-6e7fb4c5674c4eb19d3cd69845b1422c
Source dataset
uspto-grants-1986_05
Patent number
US04589911

Reaction notes

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