Stannous chloride dihydrate → 5-Tert-butyl-2-methoxy-3-methylsulphanylmethyl-aniline

HRID 1844602Notes

Reaction equation

HRID 1844602 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-])=O)[C:8]([O:14][CH3:15])=[C:9]([CH2:11][S:12][CH3:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl>C(O)C>[C:1]([C:5]1[CH:10]=[C:9]([CH2:11][S:12][CH3:13])[C:8]([O:14][CH3:15])=[C:7]([CH:6]=1)[NH2:16])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 584939255-Tert-butyl-2-methoxy-1-methylsulphanylmethyl-3-nitro-benzene

Product 1

HCID 672169135-Tert-butyl-2-methoxy-3-methylsulphanylmethyl-aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.00 g 5-tert-butyl-2-methoxy-1-methylsulphanylmethyl-3-nitro-benzene, 4.20 g tin dichloride dihydrate and 15 ml of ethanol is refluxed for 2 h. Then the solvent is removed, and water and dichloromethane are added to the residue. The mixture is filtered through Celite, and the aqueous part of the filtrate is separated off and extracted twice with dichloromethane. The combined organic phases are dried (Na2SO4), and the solvent is removed. The residue is chromatographed on aluminium oxide with cyclohexane/ethyl acetate (4:1→1:4) as eluant.

Workup

  1. temperatureis refluxed for 2 h
  2. customThen the solvent is removed
  3. additionwater and dichloromethane are added to the residue
  4. filtrationThe mixture is filtered through Celite
  5. customthe aqueous part of the filtrate is separated off
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe combined organic phases are dried (Na2SO4)
  8. customthe solvent is removed
  9. customThe residue is chromatographed on aluminium oxide with cyclohexane/ethyl acetate (4:1→1:4) as eluant

Sources & evidence

ORD record
ord-c218c5992d374d66bf32430666fce0aa
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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