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

HRID 225055Notes

Reaction equation

HRID 225055 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=O.[C:7]1([NH2:14])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[NH2:1][CH2:5][CH2:4][CH2:3][C:2]1[NH:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:14]=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

A mixture of 2-pyrrolidone (42.5 g; 0.5 mole) and o-phenylenediamine (54 g; 0.5 mole) was heated with p-toluenesulfonic acid (4.3 g) at 195°-207° for 6 hrs. while removing water (8.5 g) by distillation. A virtually quantitative yield of 2-(3-aminopropyl)benzimidazole was obtained.

Workup

  1. customwhile removing water (8.5 g)
  2. distillationby distillation

Sources & evidence

ORD record
ord-4dbeed3a99d447e5a08209c4dd0d58aa
Source dataset
uspto-grants-1980_11
Patent number
US04235838

Reaction notes

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