Ethyl Acetate → (NE)-N-(6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-ylidene)-2-methylpropane-2-sulfinamide

HRID 656500Notes

Reaction equation

HRID 656500 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][C:6](=O)[C:5]=12.[CH3:11][C:12]([S:15]([NH2:17])=[O:16])([CH3:14])[CH3:13].C(OCC)(=O)C>[Cl-].[Na+].O.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH:1]1[N:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7]/[C:6](=[N:17]\[S:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])/[C:5]=12

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 167520695H,6H,7H,8H-imidazo(1,5-a)pyridin-8-one

Product 1

HCID 141614325(NE)-N-(6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-ylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridine-8-one [426219-51-4] and 1.2 mmol of 2-methyl-propan-2-sulphinic acid amid is treated dropwise with 0.35 ml of titanium-tetra-isopropoxide. The reaction mixture is stirred at room temperature for 36 hours, then poured into 5 ml of brine and 10 ml of ethyl acetate and stirred vigorously for 10 minutes. The reaction mixture is filtered over Hyflo and the filtrate is evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. stirringstirred vigorously for 10 minutes
  2. filtrationThe reaction mixture is filtered over Hyflo
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-3f1c126959ed4c08be693a3494fddd92
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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