1-Isocyanato-4-methoxybenzene → HCID 1485415, compound

HRID 2045920Notes

Reaction equation

HRID 2045920 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:2]3[CH:3]=[N:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[CH:12]=2)=[O:28])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 1485415HCID 1485415, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 10 mmol) in hot toluene, 4-methoxyphenyl isocyanate (1.42 g, 10 mmol) was added and the reaction mixture was heated at reflux for 2 hrs. The mixture was cooled to room temperature, the resulting precipitate was filtered, washed with hexane and dried to afford 1-(4-methoxyphenyl)-3-[3-(quinoxalin-2-yl)phenyl]urea (2.3 g, 62% yield). LCMS calculated for C22H18N4O2 (M+H): 370.41. found 371. 1H-NMR (DMSO-d6, 250 Mhz) δH: 9.52 (1H, s), 8.95 (1H, br. s), 8.55 (1H, br. s), 8.42 (1H, m), 8.20-8.10 (2H, m), 7.96-7.80 (3H, m), 7.75-7.65 (1H, m), 7.55-7.46 (1H, m), 7.45-7.35 (2H, m), 6.92-6.85 (2H, m), 3.72 (3H, s).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hrs
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-74957e6107ee4d6b9e603aab18e5d9b7
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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