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Sulfuric acid magnesium salt (1:1) → (2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-(4-formylthiazol-2-ylthio)acetamide

HRID 545117
Notes
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Reaction equation

HRID 545117 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:24])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][OH:23])[N:21]=2)[CH2:7]1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:24])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH:22]=[O:23])[N:21]=2)[CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)2×HCID 67169032(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-[4-(hydroxymethyl)thiazol-2-ylthio]acetamide

Product 1

HCID 86616376(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-(4-formylthiazol-2-ylthio)acetamide

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×
HCID 6212
Chloroform
Solvent

Procedure

The resultant product (1.53 g) of (70-1) was dissolved in chloroform (10 mL), magnesium sulfate (500 mg) was added, manganese dioxide (1.35 g) was further added, and the mixture was stirred overnight at room temperature. Magnesium sulfate (500 mg) and manganese dioxide (1.35 g) were further added and the mixture was stirred at room temperature for 7 hrs. The reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (643 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 7 hrs
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography
  5. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-0be846eb0e0e405da4a9664bff148cc4
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935700B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes