Ethyl Acetate → 1-(3-Chloro-propyl)-3-(4-methyl-pyridin-3-yl)-urea

HRID 80164

Reaction equation

HRID 80164 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[CH3:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH2:15].C(OC(=O)C)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[CH3:8])=[O:7]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1379353-Amino-4-picolineHCID 166752Propane, 1-chloro-3-isocyanato-

Product 1

HCID 687869921-(3-Chloro-propyl)-3-(4-methyl-pyridin-3-yl)-ureaYield 100.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Chloro-3-isocyanato-propane (1.6 g, 13.87 mmol) was added dropwise to a stirred solution of 4-methyl-pyridin-3-ylamine (1 g, 9.25 mmol) in toluene (15 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was filtered, washed with toluene and dried under reduced pressure to afford 2.12 g (99.5% yield) of 1-(3-chloro-propyl)-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-9a0901e38543443595773620a15309ea
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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