Hydrochloric Acid → HCID 22932184, compound

HRID 1365031Notes

Reaction equation

HRID 1365031 reaction equation
[NH2-].[Na+].CS[C:5](=[S:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][CH:16]([CH3:20])[C:17](=[O:19])[CH3:18].Cl>C1(C)C=CC=CC=1>[CH2:7]([O:6][C:5](=[S:14])[CH2:18][C:17](=[O:19])[CH:16]([CH3:20])[CH3:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 112513-Methyl-2-butanoneHCID 24533Sodium amideHCID 341552628925-45-3

Product 1

HCID 22932184HCID 22932184, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of sodium amide (3.9 g) in toluene (150 mL) was added a mixture of dithiocarbonic acid O-benzyl ester S-methyl ester (9.9 g) and 3-methyl-2-butanone (4.3 g) at room temperature and the mixture was stirred at room temperature overnight. The reaction mixture was poured into a hydrochloric acid aqueous solution (1 mol/L, 500 mL), and the mixture was extracted with diethyl ether. 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-hexane/ethyl acetate=20/1) to give the title compound (4.6 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with diethyl ether
  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-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-52c0c57e67ac42fd907c2466d3c347fc
Source dataset
uspto-grants-2011_02
Patent number
US07888487B2

Reaction notes

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