2-Isocyanato-1-methoxy-4-methylbenzene → 3-(2-Methoxy-5-methyl-phenyl)-1-methyl-1-pyrazin-2-yl-urea

HRID 1821772Notes

Reaction equation

HRID 1821772 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[N:18]=[C:19]=[O:20].CCOC(C)=O.CCCCCC.C(Cl)Cl.CO>ClC(Cl)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[NH:18][C:19](=[O:20])[N:2]([CH3:1])[C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 41415202-Isocyanato-1-methoxy-4-methylbenzeneHCID 16767478N-Methylpyrazin-2-amineHCID 21226129Dichloromethane methanolHCID 21226206Ethyl acetate hexane

Product 1

HCID 220464313-(2-Methoxy-5-methyl-phenyl)-1-methyl-1-pyrazin-2-yl-urea

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 0.3 M stirred solution of 2-methylaminopyrazine (1 equiv.) in dichloroethane at room temperature under nitrogen was added 2-methoxy-5-methylphenylisocyanate (1 equiv.). The reaction was warmed to 80° C. overnight and then cooled to room temperature. In most cases, the product precipitated and was isolated by filtration. Alternatively the product could be isolated by silica gel chromatography using EtOAc/hexane or CH2Cl2/MeOH as eluant. 1H-NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.32 (s, 1H), 8.31 (s, 1H), 8.17 (s, 1H), 6.80 (m, 2H), 3.90 (s, 3H), 3.56 (s, 3H), 2.32 (s, 3H). LRMS (ESI, Positive) m/e 273.2 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. customIn most cases, the product precipitated
  3. customwas isolated by filtration
  4. customAlternatively the product could be isolated by silica gel chromatography

Sources & evidence

ORD record
ord-aa8f5d8d930d434f9aea99927fdcac57
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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