Hydrochloric Acid → HCID 22932184, compound

HRID 1351088Notes

Reaction equation

HRID 1351088 reaction equation
[C:1](=[S:12])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)SC.[CH3:13][CH:14]([CH3:18])[C:15](=[O:17])[CH3:16].[NH2-].[Na+].Cl>C1(C)C=CC=CC=1.O>[CH3:13][CH:14]([CH3:18])[C:15](=[O:17])[CH2:16][C:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[S:12]

Participants

7

Reactant 4

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

Product 1

HCID 22932184HCID 22932184, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of S-methyl O-benzyl dithiocarbonate (6.90 g) and 3-methylbutan-2-one (3.00 g) in toluene (20 mL) was added dropwise to a suspension of sodium amide (2.71 g) in toluene (60 mL) at 0° C. over a 5-minute period. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and the mixture was acidified by addition of 1 mol/L hydrochloric acid. The resulting mixture was extracted with diethyl ether, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1) to give the title compound (5.90 g).

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-946bf77e062e49c080fc546659a66dd5
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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