Sodium Chloride → HCID 21947668, compound

HRID 2214451Notes

Reaction equation

HRID 2214451 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[CH:19]=[CH:18][C:17]2[N:20]=[C:21]([S:23][CH3:24])[NH:22][C:16]=2[C:15]1=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:27][C:28]#[C:29][CH3:30].[Cl-].[Na+]>CN(C)C=O>[CH2:7]([N:14]1[CH:19]=[CH:18][C:17]2[N:20]=[C:21]([S:23][CH3:24])[N:22]([CH2:27][C:28]#[C:29][CH3:30])[C:16]=2[C:15]1=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 178503354HCID 178503354, compound

Product 1

HCID 21947668HCID 21947668, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.07 g (15.0 mmol) of potassium carbonate were added to a solution of 4.0 g (14.7 mmol) of 5-benzyl-2-methylsulphanyl-3,5-dihydro-imidazo[4,5-c]pyridin-4-one and 1.31 ml (15.0 mmol) of 1-bromo-2-butyne in 100 ml of dimethylformamide and stirred for one hour at ambient temperature. Then approx. 200 ml of saturated sodium chloride solution were added and the mixture was extracted three times with 50 ml of ethyl acetate. The extracts were washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel; eluant:dichloromethane with 0–2% ethanol).

Workup

  1. extractionthe mixture was extracted three times with 50 ml of ethyl acetate
  2. washThe extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-08068e80b1b2444cb5454a07c5cef326
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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