O-Phenylenediamine → 2-Benzimidazolepropanol

HRID 747294

Reaction equation

HRID 747294 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl[CH2:10][CH2:11][CH2:12][C:13](O)=[O:14]>Cl>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:10]1[CH2:11][CH2:12][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 123004-Chlorobutanoic acid

Product 1

HCID 754702-BenzimidazolepropanolYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1,2-Phenylenediamine (1.0 g, 12.0 mmol) and 4-chlorobutyric acid (1.5 mL, 15.17 mmol) were refluxed in 4N HCl (13 mL) for 16 hours under N2 to give the title compound as white solid (900 mg, 50%). 1H NMR (CD3OD) □ 2.04-2.08 (m, 2H), 2.97 (t, 2H, J=7.8 Hz), 5.64 (t, 2H, J=6.6 Hz), 7.15-7.21 (m, 2H), 7.47-7.49 (m, 2H); ES-MS m/z 177.1 (M+H).

Sources & evidence

ORD record
ord-02ce319b598d4c178f17b4aed858891f
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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