Phenylurea → p-Nitrophenyl phenylcarbamoylcarbamate

HRID 27992

Reaction equation

HRID 27992 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:13]>C1COCC1>[C:1]1([NH:7][C:8]([NH:10][C:12](=[O:13])[O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6145PhenylureaHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 13097706p-Nitrophenyl phenylcarbamoylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6.8 g. of phenylurea in 50 ml. of dry THF maintained at 0° C. under nitrogen were added 5.05 g. of p-nitrophenyl chloroformate. The reaction mixture was allowed to warm to room temperture and was stirred for about 18 hours. The mixture was evaporated to dryness and the residue dissolved in ethyl acetate. The solution was washed twice with water, twice with brine, and was filtered through sodium sulfate. The filtrate was evaporated to dryness to yield 4.9 g. of the product as a white product.

Workup

  1. additionwere added 5.05 g
  2. temperatureto warm to room temperture
  3. customThe mixture was evaporated to dryness
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe solution was washed twice with water, twice with brine
  6. filtrationwas filtered through sodium sulfate
  7. customThe filtrate was evaporated to dryness
  8. customto yield 4.9 g

Sources & evidence

ORD record
ord-f7c73e145846469f815f3d2c37bfe350
Source dataset
uspto-grants-1980_09
Patent number
US04224442

Linked notes

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