O-Phenylenediamine → 2-(2-Chloroethyl)benzimidazole

HRID 983582Notes

Reaction equation

HRID 983582 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]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 78993-Chloropropionic acid

Product 1

HCID 122162882-(2-Chloroethyl)benzimidazoleYield 32.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

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-e7b87730302e46b2922b763bdb7b2674
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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