Methyl Isocyanate → N-[3-(1,1-Dimethylethyl)-5-isoxazolyl]-N,N′-dimethylurea

HRID 436820Notes

Reaction equation

HRID 436820 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][CH3:11])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][N:13]=[C:14]=[O:15]>>[CH3:12][NH:13][C:14]([N:10]([CH3:11])[C:8]1[O:7][N:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:9]=1)=[O:15]

Participants

3

Reactant 2

HCID 12228Methyl Isocyanate2×HCID 13292903HCID 13292903, compound

Product 1

HCID 13292904N-[3-(1,1-Dimethylethyl)-5-isoxazolyl]-N,N′-dimethylureaYield 86.5%

Conditions

Temperature
80 °C

Procedure

A mixture of 3-t-butyl-5-methylaminoisoxazole (2.16 g) and methyl isocyanate (1.04 g) is heated at 80° C. in a sealed tube for 13 hours. Then, methyl isocyanate (0.40 g) is added thereto, and the resultant mixture is heated at 80° C. for 9 hours. The reaction mixture is chromatographed on a column of silica gel, whereby 1,3-dimethyl-3-(3-t-butyl-5-isoxazolyl)-urea (2.56 g) is obtained. The yield is 86.3%. IR: 1700, 1598 cm-1 (CC14).

Workup

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

Sources & evidence

ORD record
ord-fc3631dd6ec44381ac71459060b4fc8e
Source dataset
uspto-grants-1977_06
Patent number
US04028376

Reaction notes

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