Methyl Thioglycolate → HCID 18952085, compound

HRID 1492149Notes

Reaction equation

HRID 1492149 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].F[C:8]1[CH:9]=[C:10]([CH3:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].C(=O)(O)[O-].[Na+]>CO>[CH3:17][C:10]1[CH:9]=[CH:8][C:13]([N+:14]([O-:16])=[O:15])=[C:12]([S:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH:11]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 516892Sodium Bicarbonate

Product 1

HCID 18952085HCID 18952085, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl thioglycolate (3.18 g) was added to a mixture of 3-fluoro-4-nitrotoluene (4.65 g), sodium bicarbonate (3 g) and methanol (46 ml) and the mixture was heated to 70° C. for 5 hours. The mixture was cooled to ambient temperature and partitioned between diethyl ether and water. The organic phase was washed with a saturated aqueous sodium bicarbonate solution and with brine, dried (MgSO4) and evaporated. The residue was recrystallised from a mixture of diethyl ether and hexane to give methyl 2-(5-methyl-2-nitrophenylthio)acetate (6.5 g, 90%), m.p. 74°-75° C.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between diethyl ether and water
  3. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution and with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallised from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-c71ab7738b3d4226b1ae1bf4fca23427
Source dataset
uspto-grants-1994_12
Patent number
US05373007

Reaction notes

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