Ethyl Acetate → 1-(3-Chloropropyl)-3-pyridin-3-ylurea

HRID 80031Notes

Reaction equation

HRID 80031 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:14][C:10]1[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 100093-AminopyridineHCID 166752Propane, 1-chloro-3-isocyanato-

Product 1

HCID 596362321-(3-Chloropropyl)-3-pyridin-3-ylureaYield 95.45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Chloro-3-isocyanato-propane (1.897 g, 15.873 mmol) was added dropwise to a stirred solution of pyridin-3-ylamine (1 g, 10.582 mmol) in toluene (15 mL) over a period of 30 minutes at 0° C. The reaction temperature was maintained at room temperature for 6 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 2.1 g (95.45% yield) of 1-(3-chloro-propyl)-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-d4d1a80775374cbd9ee73cb847189189
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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