Hydrochloric Acid → HCID 22218215, compound

HRID 1795614Notes

Reaction equation

HRID 1795614 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[CH:21]([CH3:23])[CH3:22].Cl>CN(C=O)C.O>[Br:6][C:7]1[C:16]([OH:17])=[CH:15][C:14]2[C:13]([CH3:19])([CH3:20])[CH2:12][CH:11]=[C:10]([CH:21]([CH3:22])[CH3:23])[C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 22218246HCID 22218246, compound2×

Product 1

HCID 22218215HCID 22218215, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride 60% w/w (0.30 g, 6.8 mmol) in 20 mL of DMF under argon atmosphere was added slowly ethanethiol 98% (0.5 mL, 6.8 mmol), and the resulting solution was stirred for 15 min. A solution of 6-bromo-4-isopropyl-1,1-dimethyl-7-methoxy-1,2-dihydronaphthalene (Compound 102, 600 mg, 1.9 mmol) in 3 mL of DMF was added, and the reaction mixture was refluxed for 5 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 0.57 g (100%) of the title compound as a dark brown oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 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-b008c1989e814153ada280c87d06fa32
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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