Hydrochloric Acid → HCID 54263053, compound

HRID 2393029Notes

Reaction equation

HRID 2393029 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)=[CH:9][C:8]=1[O:20][CH3:21].[CH3:22][S:23]SC.Cl>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH2:15][C:16]([CH3:18])([CH3:19])[N:17]=2)=[C:9]([S:23][CH3:22])[C:8]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 14591298HCID 14591298, compoundHCID 178418339Butyllithium

Product 1

HCID 54263053HCID 54263053, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5M in hexane, 54 ml) was added with cooling to a stirred solution of 2-(4-chloro-3-methoxyphenyl)-4,4-dimethyloxazoline (27.0 g) in tetrahydrofuran while maintaining the temperature below -40° C. The mixture was stirred at -78° C. overnight. A solution of dimethyl disulphide (26.5 g) in tetrahydrofuran was added dropwise and the mixture was stirred at -40° C. overnight. After allowing to warm to room temperature the mixture was treated with hydrochloric acid (2M). The organic layer was washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by dry column flash chromatography eluted with a mixture of ethyl acetate and n-hexane to give 2-[4-chloro-3-methoxy-2-(methylsulphenyl) phenyl]-4,4-dimethyloxazoline (11.1 g) as a white solid, m.p. 50°-52° C.

Workup

  1. temperaturewhile maintaining the temperature below -40° C
  2. stirringthe mixture was stirred at -40° C. overnight
  3. temperatureto warm to room temperature the mixture
  4. washThe organic layer was washed with water
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified
  9. customby dry column flash chromatography
  10. washeluted with a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-d951d3d8a8dc43a5ac722473e33b685d
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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