Hydrochloric Acid → 2-Benzothiazolepentanamine

HRID 1282721Notes

Reaction equation

HRID 1282721 reaction equation
Cl.[C:2]1(=O)[NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17].[OH-].[Na+]>>[NH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1[S:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7768CaprolactamHCID 87132-AminothiophenolHCID 14798Sodium Hydroxide

Product 1

HCID 122624222-Benzothiazolepentanamine

Procedure

36.5 g of hydrogen chloride gas are introduced over a period of 30 minutes into a mixture of 113 g (1 mol) of caprolactam and 125 g (1 mol) of o-aminothiophenol, followed by the introduction of another 20 g of hydrogen chloride gas over a period of 3 hours at 160°C. The melt is then stirred into a mixture of 200 g of 45 % by weight sodium hydroxide and 200 g of ice, the supernatant oil separated off and the aqueous phase extracted by shaking with 200 ml of CH2Cl2. The combined organic phases are concentrated in vacuo and subsequently subjected to fractional distillation, giving 194 g (88 % of the theoretical) of 2-(5'-aminopentyl)-benzthiazole in the form of a yellowish oil with a boiling point of 131° to 133°C at 0.05 Torr.

Workup

  1. customthe supernatant oil separated off
  2. extractionthe aqueous phase extracted
  3. concentrationThe combined organic phases are concentrated in vacuo
  4. distillationsubsequently subjected to fractional distillation

Sources & evidence

ORD record
ord-71acaba0c3204bb2a59f2318881d48dd
Source dataset
uspto-grants-1976_08
Patent number
US03972890

Reaction notes

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