p-Toluenesulfonic acid → 1H-Benzimidazole-2-pentanamine

HRID 1282718Notes

Reaction equation

HRID 1282718 reaction equation
[C:1]1(=O)[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1([NH2:16])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]1[NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7243O-PhenylenediamineHCID 7768Caprolactam

Product 1

HCID 1623871H-Benzimidazole-2-pentanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 678 g (6 mols) of caprolactam, 865 g (8 mols) of o-phenylene diamine and 60 g of p-toluene sulphonic acid is melted in a nitrogen atmosphere, 108 g of water distilling off over a period of 6 hours at an internal temperature of 200° to 250°C. The reaction mixture is then subjected to fractional distillation under reduced pressure, giving 1003 g (82.4 % of the theoretical) of 2-(5'-aminopentyl)- benzimidazole with boiling point of 210° to 215°C at 0.05 Torr, and a melting point of 101°C.

Workup

  1. distillationThe reaction mixture is then subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-9ba27664358e4d259b81fe45d2bff823
Source dataset
uspto-grants-1976_08
Patent number
US03972890

Reaction notes

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