Phenyl isocyanate → N-(Dihydro-2-oxo-2H-1,3-oxazin-3(4H)-yl)-N′-phenylurea

HRID 437939Notes

Reaction equation

HRID 437939 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][O:4][C:3]1=[O:8].C(COC)OC.[C:15]1([N:21]=[C:22]=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC>[O:8]=[C:3]1[N:2]([NH:1][C:22]([NH:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:23])[CH2:7][CH2:6][CH2:5][O:4]1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 80711,2-DimethoxyethaneHCID 214274133-Amino-1,3-oxazinan-2-one

Product 1

HCID 15135399N-(Dihydro-2-oxo-2H-1,3-oxazin-3(4H)-yl)-N′-phenylureaYield 53%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 5.4 g of 3-amino-tetrahydro-1,3-oxazine-2-one and 50 ml glyme was added 5.0 ml of phenyl isocyanate. After an exothermic reaction a white solid formed. The mixture was refluxed for 1 hr, cooled, diluted with hexane and filtered. The solid product was crystallized from 200 ml of ethanol to give 5.8 g (53% yield) of white cotton-like needles of 1-(tetrahydro-2-oxo-1,3-oxazin-3-yl)-3-phenylurea, mp 204°-207°.

Workup

  1. customAfter an exothermic reaction a white solid
  2. customformed
  3. temperatureThe mixture was refluxed for 1 hr
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe solid product was crystallized from 200 ml of ethanol

Sources & evidence

ORD record
ord-c2d7d7b2ad104bc1b0bac457ff90adb3
Source dataset
uspto-grants-1977_06
Patent number
US04032638

Reaction notes

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