Sodium Carbonate → N-(3-Methyl-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea

HRID 280446Notes

Reaction equation

HRID 280446 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH3:5][C:6]1[S:7](=[O:21])(=[O:20])[O:8][C:9]2[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][CH:13]=[CH:12][C:10]=2[CH:11]=1.N12CCCN=C1CCCCC2.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:5][C:6]1[S:7](=[O:21])(=[O:20])[O:8][C:9]2[C:15]([S:16]([NH:17][C:3]([NH:2][CH3:1])=[O:4])(=[O:19])=[O:18])=[CH:14][CH:13]=[CH:12][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 12228Methyl IsocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135920743-Methyl-8-sulfamoyl-2,2-dioxo-1,2-benzoxathiine

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.15 g of methyl isocyanate are added dropwise at 0° C. to a solution of 5.5 g of 3-methyl-8-sulfamoyl-2,2-dioxo-1,2-benzoxathiine and 3.2 g of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture is stirred for 2 hours at 20°-25° C., then diluted with water, neutralised with 5% sodium carbonate solution and filtered. The filtrate is acidified and 5.4 g of N-(3-methyl-2,2-dioxo-1,2-benzoxathiin-8-yl-sulfonyl)-N'-methylurea precipitate. This precipitate is isolated and dried.

Workup

  1. filtrationfiltered
  2. customThis precipitate is isolated
  3. customdried

Sources & evidence

ORD record
ord-12947082a5664dc6beeb61013ae178bc
Source dataset
uspto-grants-1986_05
Patent number
US04589911

Reaction notes

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