Acetic Acid → HCID 21846960, compound

HRID 619732Notes

Reaction equation

HRID 619732 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][CH3:10])=[CH:6][C:5]([S:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][N:16]=[CH:17]3)=[C:4]([Cl:22])[CH:3]=1.[C:23](O)(=O)[CH3:24].O.N>Cl>[Cl:22][C:4]1[C:5]([S:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][N:16]=[CH:17]3)=[CH:6][C:7]2[N:8]([CH2:23][CH3:24])[C:9]([CH3:10])=[N:1][C:2]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12896473Azane;hydrateHCID 21846989HCID 21846989, compound

Product 1

HCID 21846960HCID 21846960, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(4-Amino-5-ethylamino-2-chlorophenylsulfanyl)isoquinoline 210 mg (0.6 mmol) was dissolved in 6N hydrochloric acid 3 ml, acetic acid 0.1 ml was added, and the mixture was heated and refluxed overnight. The reaction mixture was neutralized with ammonia water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and 5-chloro-1-ethyl-6-(5-isoquinolylsulfanyl)-2-methyl-1H-benzo[d]imidazole 130 mg (58.5%) was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e9ba217aa6614c43bd597e5751ffcbe5
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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