Urea → 4-Nitrophenyl carbamoylcarbamate

HRID 27993Notes

Reaction equation

HRID 27993 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].Cl[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:7]>C(#N)C>[C:2]([NH:4][C:6](=[O:7])[O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)(=[O:3])[NH2:1]

Participants

4

Reactant 2

HCID 1176UreaHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 233411034-Nitrophenyl carbamoylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1.20 g. (20 mmole) of urea and 2.02 g. (10 mmole) of p-nitrophenyl chloroformate in a dry flask under nitrogen were added 10 ml. of dry acetonitrile. The reaction mixture momentarily became clear and then a precipitate formed. The mixture was stirred for 18 hours at room temperature and the precipitate was filtered, washed with water and dried under vacuum. The dried product was triturated with ether and redried to yield 1.0 g. of crystalline product.

Workup

  1. additionTo a mixture of 1.20 g
  2. customThe reaction mixture momentarily became clear and then a precipitate formed
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum
  6. customThe dried product was triturated with ether
  7. customredried
  8. customto yield 1.0 g

Sources & evidence

ORD record
ord-b9d03369cb3b4c729fbd92f1ce219f8c
Source dataset
uspto-grants-1980_09
Patent number
US04224442

Reaction notes

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