Hydrochloric Acid → HCID 22218237, compound

HRID 1795607Notes

Reaction equation

HRID 1795607 reaction equation
[H-].[Na+].C(S)C.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17]C)[C:13]([CH3:20])([CH3:19])[CH2:12][CH:11]=[C:10]2[CH3:21].Cl>CN(C=O)C.O>[Br:6][C:7]1[C:16]([OH:17])=[CH:15][C:14]2[C:13]([CH3:20])([CH3:19])[CH2:12][CH:11]=[C:10]([CH3:21])[C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 22218195HCID 22218195, compound2×

Product 1

HCID 22218237HCID 22218237, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride 60% w/w (0.12 g, 3.0 mmol) in 10 mL of DMF under the argon atmosphere was added slowly ethanethiol 98% (0.2 mL, 3.0 mmol), and the resulting solution was stirred for 15 min. A solution 6-bromo-7-methoxy-1,1,4-trimethyl-1,2-dihydronaphthalene (Compound 93, 0.24 g, 0.84 mmol) in 2 mL of DMF was added, and the reaction mixture was refluxed for 4 h, then cooled to room temperature, acidified with 2 N HCl, diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, and filtered. The solvent was removed to afford 0.23 g (100%) of the title compound as a clear oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-6d9c9feddcb64440a859ec1196fdb77b
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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