N-Methylbutylamine → N-Butyl-N'-(5-tert-butyl-1,2-oxazol-3-yl)-N-methylurea

HRID 1764401Notes

Reaction equation

HRID 1764401 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([N:10]=[C:11]=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][NH:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1C=CC=CC=1>[CH2:15]([N:14]([CH3:13])[C:11]([NH:10][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[O:9][N:8]=1)=[O:12])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 129188385-Tert-butyl-3-isocyanato-1,2-oxazole

Product 1

HCID 20534526N-Butyl-N'-(5-tert-butyl-1,2-oxazol-3-yl)-N-methylureaYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5-t-butyl-3-isoxazolyl isocyanate (1.99 g) in benzene (120 ml), N-methylbutylamine (1.15 g) is added, and the resultant mixture is refluxed for 3 hours. After cooling, the reaction mixture is evaporated to remove the solvent, and the residue is chromatographed on a plate of silica gel to give 1-butyl-1-methyl-3-(5-t-butyl-3-isoxazolyl)urea (2.73 g). This substance is recrystallized from hexane to give crystals melting at 65.5° to 66.5° C. The yield is 89.8%.

Workup

  1. additionis added
  2. temperatureAfter cooling
  3. customthe reaction mixture is evaporated
  4. customto remove the solvent
  5. customthe residue is chromatographed on a plate of silica gel

Sources & evidence

ORD record
ord-9bff75acc5c64be5ac6b5c778185ae63
Source dataset
uspto-grants-1978_09
Patent number
US04116671

Reaction notes

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