Tetraethylammonium → N-Methyl-N-phenylurea

HRID 441971Notes

Reaction equation

HRID 441971 reaction equation
CNC(=O)O[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:12]C1C=CC=CC=1.C([N+](CC)(CC)CC)C.[OH:28][C:29]1C=CC([N+]([O-])=O)=[CH:31][N:30]=1>C(O)C>[CH3:31][N:30]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:29]([NH2:12])=[O:28]

Participants

6

Reactant 4

HCID 5413TetraethylammoniumHCID 6115AnilineHCID 16034Phenyl MethylcarbamateHCID 178526703HCID 178526703, compound

Product 1

HCID 78316N-Methyl-N-phenylureaYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.1 g. of phenyl N-methylcarbamate, 9.3 g. of aniline and 5.4 g. of the tetraethylammonium salt of 2-hydroxy-5-nitro-pyridine are refluxed in 200 ml. of ethanol for 5 hours. The reaction solution is concentrated, and the residue is dissolved in 100 ml. of chloroform, washed successively with 50 ml. of 1N sodium carbonate, 50 ml. of 1N hydrochloric acid and 100 ml. of water, and dried. By concentrating to dryness and recrystallizing from 120 ml. of ethanol, crystals of N-methyl-N-phenylurea having a m.p. of 150° - 151° C. are obtained in 91% yield.

Workup

  1. concentrationThe reaction solution is concentrated
  2. dissolutionthe residue is dissolved in 100 ml
  3. washof chloroform, washed successively with 50 ml
  4. dry with materialof water, and dried
  5. concentrationBy concentrating to dryness
  6. customrecrystallizing from 120 ml

Sources & evidence

ORD record
ord-7a119bb21ff54d1eb77d350e75b11833
Source dataset
uspto-grants-1977_08
Patent number
US04043992

Reaction notes

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