Sodium Carbonate → N-(2,3-dihydro-2,2-dimethylbenzo[b]furan-7-ylsulfonyl)-N'-methylurea

HRID 979736Notes

Reaction equation

HRID 979736 reaction equation
N12CCCCC1C=NCCC2.[CH3:12][C:13]1([CH3:26])[O:17][C:16]2[C:18]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:19][CH:20]=[CH:21][C:15]=2[CH2:14]1.[CH3:27][N:28]=[C:29]=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH3:12][C:13]1([CH3:26])[O:17][C:16]2[C:18]([S:22]([NH:23][C:29]([NH:28][CH3:27])=[O:30])(=[O:25])=[O:24])=[CH:19][CH:20]=[CH:21][C:15]=2[CH2:14]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 12228Methyl IsocyanateHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 134241802,2-Dimethyl-2,3-dihydro-1-benzofuran-7-sulfonamide2×

Product 1

HCID 20222551N-(2,3-dihydro-2,2-dimethylbenzo[b]furan-7-ylsulfonyl)-N'-methylureaYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6.54 ml of 1,5-diazabicyclo(5,4,0)undec-5-ene are added to 9.9 g (0.0436 mole) of 2,3-dihydro-2,2-dimethyl-7-sulfamoylbenzo[b]furan (compound 1.4) in dioxan. 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 11.1 g (89.5% of theory) of N-(2,3-dihydro-2,2-dimethylbenzo[b]furan-7-ylsulfonyl)-N'-methylurea.

Workup

  1. additionare added dropwise
  2. filtrationfiltered

Sources & evidence

ORD record
ord-bcd5d32f98a747139092db933504b1a0
Source dataset
uspto-grants-1987_01
Patent number
US04634465

Reaction notes

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