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

HRID 225054Notes

Reaction equation

HRID 225054 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>>[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

4

Reactant 3

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

Product 1

HCID 1623871H-Benzimidazole-2-pentanamine

Procedure

A mixture of caprolactam (56.5 g; 0.5 mole) and o-phenylene diamine (54 g; 0.5 mole) was heated with p-toluene sulfonic acid (4.3 g; 0.025 mole) at 200°-225° for 7 hrs. under nitrogen. A quantitative yield of 2-(5-aminopentyl) benzimidazole was obtained.

Sources & evidence

ORD record
ord-bca88a66df8d41ddbacf83a453ec7cd7
Source dataset
uspto-grants-1980_11
Patent number
US04235838

Reaction notes

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