Hydrochloric Acid → HCID 22218215, compound

HRID 1166678Notes

Reaction equation

HRID 1166678 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.C(OCC)(=O)C>[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

8

Reactant 4

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

Product 1

HCID 22218215HCID 22218215, compoundYield 101.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

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 2N HCl, diluted with water andextracted 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. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-03b4c29193314156be78494cf8cf9aa4
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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