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Sulfuric acid magnesium salt (1:1) → methyl 3-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]benzoate

HRID 64449
Notes
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Reaction equation

HRID 64449 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].S([O-])([O-])(=O)=O.[Mg+2]>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[C:14]([S@@:17](/[N:19]=[CH:1]/[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:18])([CH3:16])([CH3:15])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 639145Methyl 3-formylbenzoateHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 90072367methyl 3-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]benzoateYield 61.4%

Reagents, catalysts & solvents 2

HCID 466102
Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3.0 g of methyl 3-formylbenzoate, 2.5 g of (S)-2-methyl-2-propanesulfinamide, 250 mg of pyridinium paratoluene sulfonate, and 11 g of magnesium sulfate in 50 ml of dichloromethane was stirred overnight. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 3.0 g of methyl 3-[(E)-{[(S)-tert-butylsulfinyl]imino}methyl]benzoate.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae2adc3ef3c44339aeffce4f7d770d98
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447090B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes