Methanethiol → HCID 18978007, compound

HRID 2393027Notes

Reaction equation

HRID 2393027 reaction equation
[CH3:1][SH:2].[CH3:3][C:4]1[C:5]([N+]([O-])=O)=[C:6]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:3][C:4]1[C:5]([S:2][CH3:1])=[C:6]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 11430Potassium CarbonateHCID 18978027HCID 18978027, compound

Product 1

HCID 18978007HCID 18978007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of methanethiol (22 ml) in dry dimethyl formamide was added to a mixture of ethyl 3,4-dimethyl-2-nitrobenzoate (21.54 g) and potassium carbonate (20.02 g) in dry dimethyl formamide while maintaining the temperature below -15° C. The mixture was stirred at -10° C. for 0.5 hours and at room temperature for 3 days. Water was added and the mixture was extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and hexane (8:1) to give ethyl 3,4-dimethyl-2-methylsulphenylbenzoate (21.25 g) as a clear oil, NMR (CDCl3) 1.4(t,3H), 2.3(s,3H), 2.35(s,3H), 2.55(s,3H), 4.4(q,2H), 7.1(d,1H), 7.2(d,1H).

Workup

  1. temperaturewhile maintaining the temperature below -15° C
  2. extractionthe mixture was extracted with ether
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography
  8. washeluted with a mixture of ethyl acetate and hexane (8:1)

Sources & evidence

ORD record
ord-d149dd19dc744ea5a3fd00975ddc5e83
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

Loading…