Methyl iodide → Methyl 2-(methylsulfanyl)-5-nitrobenzoate

HRID 637108Notes

Reaction equation

HRID 637108 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[CH:15](N(CC)C(C)C)(C)C.CI.C(OCC)(=O)C.CCCCCC>C(#N)C.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([O:7][CH3:15])=[O:6]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexaneHCID 234999612-(Methylthio)-5-nitrobenzoic acid

Product 1

HCID 7164673Methyl 2-(methylsulfanyl)-5-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 2-methylthio-5-nitrobenzoic acid, (3.2 g, 15 mmol), N,N-diisopropylethylamine (17.0 mL, 100 mmol), and methyl iodide (12.45 mL, 200 mmol) in acetonitrile (50 mL). After 18 hours, dilute the reaction mixture with ethyl acetate, extract with brine, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 20% ethyl acetate/hexane to give methyl 2-methylthio-5-nitrobenzoate. Rf=0.58 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. extractionextract with brine
  2. dry with materialdry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue

Sources & evidence

ORD record
ord-5ee474a1478f4586b8b1558a32026506
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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