Methylamine → Urea, N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-N'-methyl-

HRID 436819Notes

Reaction equation

HRID 436819 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([N:10]=[C:11]=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][NH2:14]>C1(C)C=CC=CC=1>[CH3:13][NH:14][C:11]([NH:10][C:8]1[O:7][N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=1)=[O:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13292893HCID 13292893, compound

Product 1

HCID 3237157Urea, N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-N'-methyl-Yield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 3-t-butyl-5-isoxazolyl isocyanate (2.84 g) in toluene (51 ml) is introduced methylamine (1.58 g) at room temperature. The mixture is stirred at room temperature for 2 hours and then at 50° C. for 4 hours. The reaction mixture is evaporated to remove the solvent, and the residue is recrystallized from ethyl acetate to give 1-methyl-3-(3-t-butyl-5-isoxazolyl)urea (2.80 g) as crystals melting at 195.0° to 196.0° C. (decomp.). The yield is 83.6%.

Workup

  1. waitat 50° C. for 4 hours
  2. customThe reaction mixture is evaporated
  3. customto remove the solvent
  4. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c5dc2703ebca4799ae08d53ffb0806ff
Source dataset
uspto-grants-1977_06
Patent number
US04028376

Reaction notes

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