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Hydrochloric Acid → HCID 22932184, compound

HRID 1351088
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 112513-Methyl-2-butanoneHCID 24533Sodium amideHCID 3415526O-Benzyl S-methyl dithiocarbonate

Product 1

HCID 22932184HCID 22932184, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217697B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes