Hydrochloric Acid → HCID 23031161, compound

HRID 1766644Notes

Reaction equation

HRID 1766644 reaction equation
CN(C)C(=O)[S:4][C:5]1[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2.[OH-].[Na+].Cl>CO>[CH3:14][C:13]1[CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:5]=1[SH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86597597HCID 86597597, compound

Product 1

HCID 23031161HCID 23031161, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of S-(5-methyl-7-nitroindan-4-yl) dimethylthiocarbamate (5.0 g) in a 2 mol/L aqueous solution of sodium hydroxide (30 mL) and methanol (30 mL) was stirred at 90° C. under an argon atmosphere for 6 hours. The reaction mixture was cooled to room temperature. The reaction mixture was acidified by 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1−3/1) to give the title compound (1.87 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1−3/1)

Sources & evidence

ORD record
ord-1c7bd8802d164b46912e3c06ffb877ff
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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