Sodium methanethiolate → 4-Methylsulfanyl-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester

HRID 1810834Notes

Reaction equation

HRID 1810834 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([N+]([O-])=O)=[C:6]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH:5]=1.[CH3:24][S-:25].[Na+]>CN1CCN(C)C1=O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([S:25][CH3:24])=[C:6]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 67076436HCID 67076436, compound

Product 1

HCID 670767584-Methylsulfanyl-3-(2-m-tolyl-ethoxy)-benzoic acid methyl esterYield 66.5%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

The compound of step 1 (900 mg, 2.85 mmol) was dissolved in 1,3-dimethyl-2-imidazolidinone (6 ml), and sodium methanethiolate (0.23 g, 3.29 mmol) was added. The mixture was reacted at room temperature for 60 h, then partitioned between a saturated sodium chloride solution and EA, and the aqueous phase extracted with EA. The organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to give 600 mg of the title compound.

Workup

  1. customThe mixture was reacted at room temperature for 60 h
  2. custompartitioned between a saturated sodium chloride solution and EA
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-20294b4177ce4c8dae6b5822ee6a9aef
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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