p-Toluenesulfonic acid → 3-(1H-1,3-benzodiazol-2-yl)propan-1-amine

HRID 1282720Notes

Reaction equation

HRID 1282720 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[NH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[NH2:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7243O-PhenylenediamineHCID 120252-Pyrrolidone

Product 1

HCID 17131513-(1H-1,3-benzodiazol-2-yl)propan-1-amine

Procedure

162 g (1.5 mols) of o-phenylene diamine, 85 g (1 mol) of pyrrolidone and 8 g of p-toluene sulphonic acid are melted, while stirring, in a nitrogen atmosphere and the water which is gradually eliminated is distilled off over a period of 5 hours at a sump temperature of 150° to 250°C. The reaction mixture is then subjected to fractional distillation under reduced pressure. 150 g (85.5 % of the theoretical) of 2-(3'-aminopropyl)-benzimidazole are obtained at a pressure of 0.1 Torr and a boiling temperature of 190° to 196°C in the form of a brownish-yellow crystalline mass melting at 118°C.

Workup

  1. distillationthe water which is gradually eliminated is distilled off over a period of 5 hours at a sump temperature of 150° to 250°C
  2. distillationThe reaction mixture is then subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-8ceb352d4f5c44dd8ae471047a45f5d5
Source dataset
uspto-grants-1976_08
Patent number
US03972890

Reaction notes

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