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

HRID 80271

Reaction equation

HRID 80271 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].[Cl:9][CH2:10][C:11]([N:14]=[C:15]=[O:16])([CH3:13])[CH3:12].CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:9][CH2:10][C:11]([NH:14][C:15]([NH:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:16])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 1379353-Amino-4-picolineHCID 110407471-Chloro-2-isocyanato-2-methyl-propane

Product 1

HCID 687856051-(2-Chloro-1,1-dimethyl-ethyl)-3-(4-methyl-pyridin-3-yl)-ureaYield 97.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

4-Methyl-pyridin-3-ylamine (1.98 g, 18.33 mmol) was added to solution of 1-chloro-2-isocyanato-2-methyl-propane (I-200c: 3 g, 20.40 mmol) in toluene (30 mL). The resulting mixture was stirred at room temperature for 3 days. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was filtered and the residue was dried to afford 4.3 g of the product (87.75% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe residue was dried

Sources & evidence

ORD record
ord-b07c728c21cb48b78444794a121a8a1f
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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