Acetic Acid → HCID 21847004, compound

HRID 619736Notes

Reaction equation

HRID 619736 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]([NH2:26])=[CH:11][CH:12]=[C:13]([S:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]=[CH:21]3)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](O)(=O)[CH3:28].[Cl-].[Na+]>Cl>[CH2:1]([N:8]1[C:9]2[CH:14]=[C:13]([S:15][C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][N:20]=[CH:21]4)[CH:12]=[CH:11][C:10]=2[N:26]=[C:27]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 21846914HCID 21846914, compound

Product 1

HCID 21847004HCID 21847004, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N2-Benzyl-4-(5-isoquinolylsulfanyl)-1,2-benzenediamine 730 mg (2.0 mmol) was dissolved in 4N hydrochloric acid 20 ml, acetic acid 0.3 ml was added, and the mixture was heated and refluxed overnight. 40% sodium chloride was added to obtain an alkaline solution, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform: acetone=5:1), and 1-benzyl-6-(5-isoquinolylsulfanyl)-2-methyl-1H-benzo[d]imidazole 330 mg (43.3%) was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed overnight
  3. customto obtain an alkaline solution
  4. extractionthe solution was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (chloroform: acetone=5:1)

Sources & evidence

ORD record
ord-842463b4e1ee4615abafcebf968b27bd
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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