2-Bromopropane → m-Isopropylthioaniline

HRID 435742Notes

Reaction equation

HRID 435742 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Br[CH:12]([CH3:14])[CH3:13]>O1CCOCC1>[CH:12]([S:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 315773-Aminothiophenol

Product 1

HCID 18931781m-IsopropylthioanilineYield 70.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring suspension of 25 grams (0.2 mole) of 3-aminothiophenol in 200 ml. of 5N NaOH was added drop-wise a solution of 24.6 grams of 2-bromopropane (0.20 mole; M.W. 123.00) dissolved in 100 ml. of 1,4-dioxane. The resulting suspension was stirred at room temperature overnight and then was extracted with two 500 ml. portions of ethyl ether. The ether extracts were combined, dried over Na2SO4, and evaporated in vacuo to yield 23.5 grams of m-isopropylthioaniline.

Workup

  1. dissolutiondissolved in 100 ml
  2. extractionwas extracted with two 500 ml
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b983b3f81a9444ca8d912ee8180318e
Source dataset
uspto-grants-1977_02
Patent number
US04006161

Reaction notes

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