Monoisouron → N-[[[5-(1,1-Dimethylethyl)-3-isoxazolyl]amino]carbonyl]-N-methyl-1-butanesulfenamide

HRID 461361Notes

Reaction equation

HRID 461361 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:4].[CH2:15]([S:19]Cl)[CH2:16][CH2:17][CH3:18]>N1C=CC=CC=1>[CH3:1][N:2]([S:19][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]([NH:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 186687MonoisouronHCID 108554491-butanesulfenyl chloride

Product 1

HCID 20534529N-[[[5-(1,1-Dimethylethyl)-3-isoxazolyl]amino]carbonyl]-N-methyl-1-butanesulfenamideYield 10.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-methyl-3-(5-t-butyl-3-isoxazolyl)urea (1.97 g) in pyridine (30 ml), butylsulfenyl chloride (1.08 mol equivalent) is added at -30° to -40° C. The resultant mixture is allowed to stand at -30° to -40° C for 6 hours and at room temperature overnight. The reaction mixture is chromatographed on a column of silica gel, whereby 1-methyl-1-butylthio-3-(5-t-butyl-3-isoxazolyl)urea (0.31 g) is obtained as an oil. I.R.: 1698, 1606 cm-1 (CCl4).

Workup

  1. customThe reaction mixture is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-8bb7514113564c88b60854540e74662b
Source dataset
uspto-grants-1977_12
Patent number
US04062861

Reaction notes

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