Phenyl isocyanate → 1-Methyl-1-(4-pyridylmethyl)-3-phenylurea

HRID 1164511Notes

Reaction equation

HRID 1164511 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[C:17]([NH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 81436N-Methylpyridine-4-methylamine

Product 1

HCID 205111981-Methyl-1-(4-pyridylmethyl)-3-phenylureaYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(Methylaminomethyl)pyridine (5 g), dry chloroform (500 ml) and phenyl isocyanate (5 g) were stirred together at room temperature for 2 hours. The chloroform was then evaporated in vacuo and the resultant oil was redissolved in the minimum quantity of chloroform and chromatographed on a "Florisil" (Trade Mark) (100 g) column using chloroform containing gradually increasing quantities of methanol (up to 2.5%) as eluting solvent. Appropriate fractions (identified by t.l.c.) were combined and evaporated in vacuo to give 1-methyl-1-(4-pyridylmethyl)-3-phenylurea as an oil (8.0 g).

Workup

  1. customThe chloroform was then evaporated in vacuo
  2. dissolutionthe resultant oil was redissolved in the minimum quantity of chloroform
  3. customchromatographed on a "Florisil" (Trade Mark) (100 g) column
  4. washas eluting solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f2fd42d96fb419ea2fa88b7ace0ef5b
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

Loading…