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

HRID 1722189Notes

Reaction equation

HRID 1722189 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([S:12]([NH:15][C:16](NC)=[O:17])(=[O:14])=[O:13])[C:5]=2[O:4][S:3]1(=[O:21])=[O:20].C(Cl)(Cl)=O>C1C(Cl)=CC=C(Cl)C=1>[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])[C:5]=2[O:4][S:3]1(=[O:21])=[O:20]

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-ylsulfonylisocyanateYield 116.4%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

14.3 g of N-(3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea are suspended in 143 ml of dry dichlorobenzene. 9.5 g of phosgene are introduced into the mixture over 75 minutes at 140° C. Dry nitrogen is subsequently blown through the reaction mixture for 20 minutes. With the exclusion of moisture, the solution is concentrated by evaporation at 90° C./20 mbar, affording 15.1 g of 3,4-dihydro-3-methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl isocyanate in the form of an oil which is dissolved in warm absolute dioxane and, without further storage, is reacted in the subsequent step (c).

Workup

  1. concentrationWith the exclusion of moisture, the solution is concentrated by evaporation at 90° C./20 mbar

Sources & evidence

ORD record
ord-fb6a6ba9c9924ff6b1b2e56c20c46382
Source dataset
uspto-grants-1989_08
Patent number
US04854963

Reaction notes

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