Triethylamine → Monoisouron

HRID 1764399Notes

Reaction equation

HRID 1764399 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[O:4][N:3]=1.[CH3:11][N:12]=[C:13]=[O:14].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:11][NH:12][C:13]([NH:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[O:4][N:3]=1)=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 186687MonoisouronYield 91.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-amino-5-t-butylisoxazole (16.82 g) in anhydrous benzene (140 ml), methyl isocyanate (8.90 g) and triethylamine (0.5 ml) are added. The resulting mixture is stirred at room temperature for about 8 hours, allowed to stand overnight and refluxed for 1 hour. After ice cooling, the reaction mixture is filtered to give a precipitate which is recrystallized from ethyl acetate to give 1-methyl-3-(5-t-butyl-3-isoxazolyl)urea (21.61 g) as colorless needles melting at 187.0° to 187.5° C.

Workup

  1. waitto stand overnight
  2. temperaturerefluxed for 1 hour
  3. filtrationAfter ice cooling, the reaction mixture is filtered
  4. customto give a precipitate which
  5. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6863d94397f94cfd92bf17be1e358008
Source dataset
uspto-grants-1978_09
Patent number
US04116671

Reaction notes

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