Sodium Carbonate → N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea

HRID 653520Notes

Reaction equation

HRID 653520 reaction equation
N12CCCN=C1CCCCC2.[O:12]=[S:13]1(=[O:28])[CH:18]([CH3:19])[CH2:17][C:16]2[CH:20]=[CH:21][CH:22]=[C:23]([S:24]([NH2:27])(=[O:26])=[O:25])[C:15]=2[O:14]1.[CH3:29][N:30]=[C:31]=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[O:28]=[S:13]1(=[O:12])[CH:18]([CH3:19])[CH2:17][C:16]2[CH:20]=[CH:21][CH:22]=[C:23]([S:24]([NH:27][C:31]([NH:30][CH3:29])=[O:32])(=[O:25])=[O:26])[C:15]=2[O:14]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 12228Methyl IsocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135920753,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide

Product 1

HCID 19839353N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylureaYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6.54 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene are added to 12.1 g (0.0436 mole) of 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide in dioxane. While cooling with ice, 2.65 ml of methyl isocyanate are added dropwise. The reaction mixture is stirred for 2 hours at 20° to 25° C., then diluted with water, neutralised with 10 ml of 5% sodium carbonate solution, and filtered. Acidification of the filtrate yields 12.0 g (91% of theory) of N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-methylurea.

Workup

  1. additionare added dropwise
  2. filtrationfiltered

Sources & evidence

ORD record
ord-17a7c8db7a1b4aef80c1f00f0d0722a5
Source dataset
uspto-grants-1987_06
Patent number
US04677212

Reaction notes

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