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Hydrochloric Acid → HCID 15439079, compound

HRID 1365024
Notes
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Reaction equation

HRID 1365024 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][O:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2C=CC=CC=2)=[O:22])=[CH:19][CH:18]=1.Cl>C1(C)C=CC=CC=1>[CH2:7]([O:6][C:5](=[S:14])[CH2:23][C:21]([C:20]1[CH:29]=[CH:30][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:22])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24533Sodium amideHCID 691464-MethoxybenzophenoneHCID 3415526O-Benzyl S-methyl dithiocarbonate

Product 1

HCID 15439079HCID 15439079, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a suspension of sodium amide (1.6 g) in toluene (50 mL) was added a mixture of dithiocarbonic acid O-benzyl ester S-methyl ester (4.0 g) and 4-methoxybenzophenone (3.0 g) at room temperature and the mixture was stirred at room temperature overnight. Hydrochloric acid solution (2 mol/L, 80 mL) was added to the reaction mixture and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=5/1-2/1) to give the title compound (3.4 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/dichloromethane=5/1-2/1)

Sources & evidence

ORD record
ord-d343882b5c104b7197b19e8363d0db78
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888487B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes