Methanol → 1-(2-Chloro-ethyl)-3-(4-methyl-pyridin-3-yl)-urea

HRID 80037

Reaction equation

HRID 80037 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH3:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14].CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[CH3:7])=[O:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 160352-Chloroethyl isocyanateHCID 1379353-Amino-4-picoline

Product 1

HCID 148343251-(2-Chloro-ethyl)-3-(4-methyl-pyridin-3-yl)-ureaYield 86.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-Chloro-2-isocyanato-ethane (5.91 ml, 69.35 mmol) was added dropwise to a stirred solution of 4-methyl-pyridin-3-ylamine (5 g, 46.23 mmol) in toluene (180 mL) at 0° C. The reaction temperature was maintained at room temperature for 5 hours. The reaction was monitored by TLC (5% MeOH in chloroform). The reaction mixture was filtered, washed with toluene and dried under reduced pressure to afford 8.5 g (86% yield) of 1-(2-chloro-ethyl)-3-(4-methyl-pyridin-3-yl)-urea.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-30b9272dcda744cebc823dc473c6935a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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