Methyl isothiocyanate → 1-methyl-3-(3-quinoxalin-2-ylphenyl)thiourea

HRID 2045921Notes

Reaction equation

HRID 2045921 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][N:19]=[C:20]=[S:21]>C1(C)C=CC=CC=1>[CH3:18][NH:19][C:20]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[S:21]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 14854161-methyl-3-(3-quinoxalin-2-ylphenyl)thioureaYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 10 mmol) in hot toluene (80 mL), methyl isothiocyanate (0.73 g, 10 mmol) was added and the reaction mixture was heated overnight at reflux. The mixture was cooled to room temperature, the resulting precipitate was filtered to afford 1-methyl-3-[3-(quinoxalin-2-yl)phenyl]thiourea (2.0 g, 68% yield). LCMS calculated for C16H14N4S (M+H): 295.38. found 295. 1H-NMR (DMSO-d6, 250 Mhz) δH: 9.85 (1H, br. s), 9.55 (1H, s), 8.40-8.30 (1H, m), 8.20-8.00 (3H, m), 7.98-7.80 (3H, m), 7.70-7.60 (1H, m), 7.60-7.45 (1H, m).

Workup

  1. temperaturethe reaction mixture was heated overnight
  2. temperatureat reflux
  3. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-1f41f6936baa45a491cc3b5d621d3670
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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