Ethyl Acetate → N-(2-Chloroethyl)-N'-(3-pyridinyl)urea

HRID 80021Notes

Reaction equation

HRID 80021 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:13][C:9]1[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 100093-AminopyridineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 256330N-(2-Chloroethyl)-N'-(3-pyridinyl)ureaYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Chloro-2-isocyanato-ethane (560 mg, 5.31 mmol) was added dropwise to a stirred solution of pyridin-3-ylamine (500 mg, 5.31 mmol) in toluene (10 mL) over a period of 30 minutes at 0° C. The reaction temperature was maintained at room temperature for 5 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was filtered, washed with toluene and dried under reduced pressure to afford 1.0 g (98% yield) of 1-(2-Chloro-ethyl)-3-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-da10c2bddfce4b26b17fa1e21c0f001a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…