Sulfuric Acid → HCID 21873976, compound

HRID 723380Notes

Reaction equation

HRID 723380 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.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:20][C:18]1[N:19]=[C:3]2[C:2]3[NH:1][CH:10]([C:11]4[CH:15]=[CH:14][S:13][CH:12]=4)[CH2:9][C:8](=[O:16])[C:7]=3[CH:6]=[CH:5][N:4]2[C:17]=1[CH3:21]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 69586325HCID 69586325, compound

Product 1

HCID 21873976HCID 21873976, compoundYield 69.2%

Procedure

2.6 g of 8-amino-2,3-dimethyl-7-[3-(3-thienyl)-1-oxo-2-propenyl]imidazo[1,2-a]pyridine are treated at room temperature with 20 ml of aqueous 70% strength sulfuric acid, poured onto ice water (100 ml) after 90 minutes, neutralized with aqueous 6 N sodium hydroxide solution and extracted three times with 50 ml of methylene chloride each time. The combined organic phases are washed with water, dried over sodium sulfate, the solvent is stripped off in vacuo and the remaining yellow oil is stirred with 15 ml of diethyl ether. The yellowish solid obtained here is filtered off and dried in vacuo. 1.8 g of the title compound of m.p. 176–77° C. (diethyl ether) are obtained.

Workup

  1. additionpoured onto ice water (100 ml) after 90 minutes
  2. extractionextracted three times with 50 ml of methylene chloride each time
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe yellowish solid obtained here
  6. filtrationis filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3dcf0cf7a6f941728d2866f87ed4de9b
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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