Water → Phenyl 4-(methylcarbamoyl)phenylcarbamate

HRID 1871150Notes

Reaction equation

HRID 1871150 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].O>O1CCOCC1>[CH3:1][NH:2][C:3]([C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:15](=[O:16])[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 2355164-Amino-N-methylbenzamide

Product 1

HCID 18321944Phenyl 4-(methylcarbamoyl)phenylcarbamateYield 94.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 4-(methylcarbamoyl)aniline (1.0 g) in 1,4-dioxane (10 ml) were added 1N sodium hydroxide solution (13.4 ml) and phenyl chloroformate (1.26 g) under ice-cooling, and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was poured into water and extracted with a mixture of chloroform and methanol. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate to give phenyl 4-(methylcarbamoyl)phenylcarbamate (1.70 g) as pale yellow crystals.

Workup

  1. temperaturecooling
  2. extractionextracted with a mixture of chloroform and methanol
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2dc9156c1b5645b09d8526f4a3c39d0e
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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