O-Phenylenediamine → 2-(2-Chloroethyl)benzimidazole
Reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][CH2:10][CH2:11][C:12](O)=O>Cl>[Cl:9][CH2:10][CH2:11][C:12]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1,2-Phenylenediamine (1.3 g, 12.0 mmol) and 3-chloropropionic acid (2.0 g, 18.5 mmol) were refluxed in 4N HCl (13 mL) for 16 hours to give the title compound as white solid (700 mg, 32%). 1H NMR (CD3OD) □ 3.35 (t, 2H, J=6.8 Hz), 4.00 (t, 2H, J=6.8 Hz), 7.18–7.25 (m, 2H), 7.49–7.55 (m, 2H); ES-MS m/z 181.0 (M+H).
Sources & evidence
- ORD record
- ord-708aa2cb8cff44d5bab91807ea9877e3
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084155B2
Reaction notes
Loading…