Ethanol → HCID 68641311, compound

HRID 1498963Notes

Reaction equation

HRID 1498963 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[C:7]3[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:8]=3[N:9]=[C:2]12.S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[C:7]3[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:22][CH3:23])=[O:15])=[CH:10][C:8]=3[N:9]=[C:2]12

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 68642024HCID 68642024, compound

Product 1

HCID 68641311HCID 68641311, compoundYield 84%

Procedure

In ethanol (200 ml), 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylic acid (2.94 g, 13.53 mmol) prepared in the Step 38-1-4 was suspended. Concentrated sulfuric acid (10 ml) was added thereto, and the mixture was heated under reflux for 72 hours. After being allowed to cool, the mixture was concentrated under a reduced pressure. The concentrate was neutralized with a saturated sodium bicarbonate solution and 25% ammonia water and then subjected to extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (2.78 g, 84%) as a light-yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 72 hours
  3. temperatureto cool
  4. concentrationthe mixture was concentrated under a reduced pressure
  5. extractionsubjected to extraction with chloroform
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-1af817bebd764d598701fea8ca2599d3
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

Loading…