Phosgene → 3,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonylisocyanate

HRID 653521Notes

Reaction equation

HRID 653521 reaction equation
[O:1]=[S:2]1(=[O:21])[CH:7]([CH3:8])[CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13]([NH:16][C:17](NC)=[O:18])(=[O:15])=[O:14])[C:4]=2[O:3]1.C(Cl)(Cl)=O>ClC1C=CC=CC=1>[O:21]=[S:2]1(=[O:1])[CH:7]([CH3:8])[CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 19839353N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea

Product 1

HCID 198393593,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonylisocyanate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

10 g of N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea are dispersed in 400 ml of absolute chlorobenzene and the dispersion is saturated with phosgene at about 130° C., whereupon a clear solution forms. The solvent is then distilled off in vacuo, with the exclusion of moisture, to give 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonylisocyanate in the form of an oil, which can be used without further purification for obtaining the fused N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the formula I.

Workup

  1. distillationThe solvent is then distilled off in vacuo, with the exclusion of moisture

Sources & evidence

ORD record
ord-c6886cf7738e4017a2e92454e8712fca
Source dataset
uspto-grants-1987_06
Patent number
US04677212

Reaction notes

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