Hydrochloric Acid → HCID 21873953, compound

HRID 723397Notes

Reaction equation

HRID 723397 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:16])[CH:9]=[CH:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1.[OH-:22].[Na+].OO.Cl>C(O)C>[NH2:1][C:2]1[C:3]2[N:4]([C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:16])[CH:9]1[O:22][CH:10]1[C:11]1[CH:15]=[CH:14][S:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 69586325HCID 69586325, compound

Product 1

HCID 21873953HCID 21873953, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2.6 9 of 8-amino-2,3-dimethyl-7-[3-(3-thienyl)-1-oxo-2-propenyl]imidazo[1,2-a]pyridine in 80 ml of ethanol is treated successively with 5.2 ml of 6 N aqueous sodium hydroxide solution and 5 ml of 30% strength aqueous hydrogen peroxide solution, stirred at room temperature for 48 hours, poured onto 200 ml of ice water and adjusted to pH 7–8 with semisatd. aqueous hydrochloric acid. The mixture is then extracted three times with 100 ml of dichloromethane each time, the combined organic phases are washed once with saturated sodium thiosulfate solution and once with 100 ml of distilled water, the solvent is stripped off in vacuo and the residue is purified on silica gel (eluent:methylene chloride/methanol=100/3). 1.2 g of the title compound of m.p. 186–89° C. (diethyl ether) are obtained.

Workup

  1. extractionThe mixture is then extracted three times with 100 ml of dichloromethane each time
  2. washthe combined organic phases are washed once with saturated sodium thiosulfate solution and once with 100 ml of distilled water
  3. customthe residue is purified on silica gel (eluent:methylene chloride/methanol=100/3)

Sources & evidence

ORD record
ord-171c934231f940f6b9ed749f6e6c25ad
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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