Benzothiazole → 2-(3-Aminopropylthio)-aniline

HRID 126964

Reaction equation

HRID 126964 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].Cl[CH:13](C)[CH2:14][NH2:15].Cl>O.CO>[NH2:15][CH2:14][CH2:13][CH2:2][S:1][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3]

Participants

6

Reactant 3

HCID 7222BenzothiazoleHCID 14798Sodium Hydroxide2×HCID 1458552-Chloropropan-1-amine hydrochloride

Product 1

HCID 202885632-(3-Aminopropylthio)-aniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

270 parts of benzothiazole and 160 parts of sodium hydroxide are boiled under reflux for 3 hours in 400 parts of water. After cooling to 70° C., 250 parts of methanol are added, followed by the dropwise addition over a period of 2 hours at 70° C. of a solution of 260 parts of 2-chloropropylamine·HCl in 500 parts of water. After stirring for another 3 hours at 100° C., the mixture is cooled and a solution of 100 parts of sodium hydroxide in 200 parts of water is added to it. The organic phase is separated off, the aqueous phase is washed twice with 200 parts of toluene and the combined organic phases are concentrated by evaporation, leaving 346 parts of 2-(3-aminopropylthio)-aniline in the form of a yellowish liquid boiling at 130° C./0.04 mm.

Workup

  1. temperaturethe mixture is cooled
  2. customThe organic phase is separated off
  3. washthe aqueous phase is washed twice with 200 parts of toluene
  4. concentrationthe combined organic phases are concentrated by evaporation

Sources & evidence

ORD record
ord-a8eb211dc1a9495db2f7b22432defe2f
Source dataset
uspto-grants-1981_03
Patent number
US04254229

Linked notes

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