Isopropyl isocyanate → N-(5-tert-Butyl-1,2-oxazol-3-yl)-N'-propan-2-ylurea

HRID 615528Notes

Reaction equation

HRID 615528 reaction equation
[CH3:1][CH:2]([N:4]=[C:5]=[O:6])[CH3:3].[NH2:7][C:8]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[O:10][N:9]=1>O1CCCC1>[CH3:1][CH:2]([NH:4][C:5]([NH:7][C:8]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[O:10][N:9]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanate2×HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 13393045N-(5-tert-Butyl-1,2-oxazol-3-yl)-N'-propan-2-ylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.5 g of 1-methylethyl isocyanate was added to a stirred mixture of 6.2 g of 1A and 75 ml of tetrahydrofuran at room temperature, then the mixture was stirred at reflux temperature for 24 hours, when an additional 7.5 g of 1-methylethyl isocyanate was added and the mixture was stirred at reflux temperature for 24 hours. The mixture was concentrated to dryness to give a syrup. On standing overnight at room temperature, a solid formed. The solid was recrystallized from ether/hexane to give 1-(1-methylethyl)-3-(5-(1,1-dimethylethyl)-isoxazol-3-yl)urea (4A), as an off-white solid, m.p.: 135°-138° C.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. stirringthe mixture was stirred
  3. temperatureat reflux temperature for 24 hours
  4. concentrationThe mixture was concentrated to dryness
  5. customto give a syrup
  6. customa solid formed
  7. customThe solid was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-2a6d6ee25207412eb37732c9e936ce9d
Source dataset
uspto-grants-1985_02
Patent number
US04500345

Reaction notes

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