Methanol → N-(4-chlorophenyl)-N'-2-butanesulfonylurea

HRID 1586843Notes

Reaction equation

HRID 1586843 reaction equation
[CH3:1][CH:2]([S:5]([NH2:8])(=[O:7])=[O:6])[CH2:3][CH3:4].CO.C[O-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>O1CCCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:8][S:5]([CH:2]([CH2:3][CH3:4])[CH3:1])(=[O:7])=[O:6])=[O:23])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 76934-Chlorophenyl IsocyanateHCID 10942334Sodium MethoxideHCID 20482438Butane-2-sulfonamide

Product 1

HCID 9838965N-(4-chlorophenyl)-N'-2-butanesulfonylureaYield 18.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 10 was followed with 2-butanesulfonamide (6.85 g), methanol (250 ml), sodium methoxide (2.7 g), tetrahydrofuran (250 ml) and 4-chlorophenyl isocyanate (7.7 g) with the resulting solid being recrystallized from ethyl acetate to give 2.7 g of white crystals with a melting point of 172°-174° C.

Workup

  1. custombeing recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7866d7a81252482ab9e86f90ebd8102e
Source dataset
uspto-grants-1993_06
Patent number
US05216026

Reaction notes

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