Toluene → 2-((Thiophen-2-ylmethyl)thio)ethan-1-amine

HRID 848793Notes

Reaction equation

HRID 848793 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][SH:7].[OH-].[K+].Cl.Cl[CH2:12][CH2:13][NH2:14].C1(C)C=CC=CC=1>O>[NH2:14][CH2:13][CH2:12][S:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 80408Thenyl mercaptanHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 49622502-((Thiophen-2-ylmethyl)thio)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The crude product from (a) was taken up under nitrogen in a solution of 128 g of potassium hydroxide (2.3 moles) in 150 ml of water. A solution of 88.2 g (0.76 mole) of 2-chloroethyl amine hydrochloride in 100 ml of water was then added dropwise with stirring at 323° K. After 3 hours on a steam bath, the reaction mixture was taken up with 200 ml of toluene, the toluene phase was washed with 200 ml of water, dried with sodium chloride, concentrated and fractionated in vacuo.

Workup

  1. washthe toluene phase was washed with 200 ml of water
  2. dry with materialdried with sodium chloride
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d52a5a3924ae43f896738efe8fd95083
Source dataset
uspto-grants-1981_10
Patent number
US04297439

Reaction notes

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