Benzyl Bromide → 3-(Benzylsulfanyl)aniline

HRID 435743Notes

Reaction equation

HRID 435743 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1>[CH2:12]([S:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 315773-Aminothiophenol

Product 1

HCID 118443953-(Benzylsulfanyl)anilineYield 95.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring suspension of 25 grams (0.20 mole; M.W. 125.19) of 3-aminothiophenol in 200 ml. of 5N NaOH was added dropwise a solution of 34.2 grams of α-bromotoluene (0.20 mole; M.W. 171.04) dissolved in 100 ml. of 1,4-dioxane. The addition required about 30 minutes. The reaction mixture was stirred at room temperature for 2 hours and then extracted with two 500 ml. portions of ethyl ether. The extracts were combined, dried over Na2SO4, and evaporated to yield 41.0 grams of m-benzylthioaniline.

Workup

  1. dissolutiondissolved in 100 ml
  2. additionThe addition required about 30 minutes
  3. extractionextracted with two 500 ml
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-57877e9203654f38a0b315a63f7b4405
Source dataset
uspto-grants-1977_02
Patent number
US04006161

Reaction notes

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