p-Toluenesulfonic acid → 2-Benzothiazolepentanamine

HRID 225056Notes

Reaction equation

HRID 225056 reaction equation
[C:1]1(=O)[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].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[S:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7768CaprolactamHCID 87132-Aminothiophenol

Product 1

HCID 122624222-Benzothiazolepentanamine

Procedure

A mixture of caprolactam (62 g; 0.55 mole) and o-aminothiophenol (68.8; 0.55 mole) was heated with p-toluenesulfonic acid (4.3 g) at 190°-260° for 41/2 hrs. while removing water by distillation. The product was essentially pure 2-(5-aminopentyl)benzothiazole.

Workup

  1. customwhile removing water
  2. distillationby distillation

Sources & evidence

ORD record
ord-3a453a7dc5394ab0ae3406e86f63ee3b
Source dataset
uspto-grants-1980_11
Patent number
US04235838

Reaction notes

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