Methanol → 1-(2-Chloroethyl)-3-(2-methylquinolin-4-yl)urea

HRID 2223690Notes

Reaction equation

HRID 2223690 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[Cl:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18].CO>C1COCC1>[Cl:13][CH2:14][CH2:15][NH:16][C:17]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1)=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 160352-Chloroethyl isocyanateHCID 811164-Amino-2-methylquinoline

Product 1

HCID 23443661-(2-Chloroethyl)-3-(2-methylquinolin-4-yl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-2-methylquinoline (12.6 g, 80 mmol) in THF (480 mL) is added 2-chloroethylisocyanate (10.2 mL, 120 mmol) at rt. The reaction mixture is stirred for 40 h at rt. MeOH (100 mL) is added, and stirring is continued an additional hour. The reaction mixture is evaporated and the residue is taken up in CH2Cl2. The organic layer is shaken with 1 N HCl (250 mL), and the resulting precipitate is collected by filtration. The solid is washed with CH2Cl2 (100 mL), saturated NaHCO3 (2×100 mL), and with water (4×100 mL). The resulting solid is dried under HV at rt for 14 h to provide the title compound.

Workup

  1. stirringstirring
  2. waitis continued an additional hour
  3. customThe reaction mixture is evaporated
  4. stirringThe organic layer is shaken with 1 N HCl (250 mL)
  5. filtrationthe resulting precipitate is collected by filtration
  6. washThe solid is washed with CH2Cl2 (100 mL), saturated NaHCO3 (2×100 mL)
  7. customThe resulting solid is dried under HV at rt for 14 h

Sources & evidence

ORD record
ord-6204cfeb886b4c278cd57fe39d781f90
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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