Sodium Chloride → Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

HRID 1870375Notes

Reaction equation

HRID 1870375 reaction equation
[CH3:1][S-:2].[Na+].[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[N+]([O-])=O)[C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5]1.[Cl-].[Na+]>CN1CCN(C)C1=O.O>[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[S:2][CH3:1])[C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 4378561Sodium methanethiolateHCID 21187961Methyl 3-cyclopentyloxy-4-nitrobenzoate

Product 1

HCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoateYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

Sodium thiomethoxide (8.05 g, 0.115 mol) is added portionwise to a stirred solution of methyl 3-cyclopentyloxy-4-nitrobenzoate (26.5 g, 0.1 mol) in N,N'-dimethylimidazolidinone (200 mL) at ambient temperature under an atmosphere of nitrogen and stirring continued for 4 hours. The mixture is then diluted with water (1200 mL) containing sodium chloride (200 g) and extracted with ethyl acetate (2×300 mL). The combined extract is washed with saturated brine (2×300 mL) and then evaporated under reduced pressure to give methyl 3-cyclopentyloxy-4-(methylthio)benzoate (24.4 g, 91.7%) as an orange brown solid which is used without further purification.

Workup

  1. extractionextracted with ethyl acetate (2×300 mL)
  2. extractionThe combined extract
  3. washis washed with saturated brine (2×300 mL)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-368bec5037024ef886a19f275e8af80c
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

Loading…