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

HRID 521434Notes

Reaction equation

HRID 521434 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-05a322d69463458f933e26fd8755de9d
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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