Acetone → N-Phenyl-N'-2-pyridinylurea

HRID 1903293

Reaction equation

HRID 1903293 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.CC(C)=O.[SH2]=N.[C:21]1([NH:27][C:28](C2C=CC=CC=2C(O)=O)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[C:21]1([NH:27][C:28]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 8471TriethylamineHCID 104392-AminopyridineHCID 178514671HCID 178514671, compound

Product 1

HCID 221427N-Phenyl-N'-2-pyridinylureaYield 54.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.5 g aminopyridin and 0.7 ml triethylamine with 5 ml acetone was added dropwise to a suspension of 1.5 g phenylcarbamoyl-benzoic acid sulfimide with 15 ml aceton, under stirring. The reaction mixture was stirred for 45 minutes at room temperature, then diluted with 100 ml water. The acetone was distilled off, the residue was cooled, and the precipitated solid product was filtered, washed with water and dried. 0.6 g 1-phenyl-3-(2-pyridyl)-urea was obtained with a melting point of 185°-186° C.

Workup

  1. stirringThe reaction mixture was stirred for 45 minutes at room temperature
  2. distillationThe acetone was distilled off
  3. temperaturethe residue was cooled
  4. filtrationthe precipitated solid product was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-68a5453750874c93b78d6537cfc727aa
Source dataset
uspto-grants-1984_03
Patent number
US04435567

Linked notes

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