Methanol → HCID 59679904, compound

HRID 1924039Notes

Reaction equation

HRID 1924039 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[N:18]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.CO.O.[SH-].[Na+]>O>[N:18]1[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[S:11][C:10]=1[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 16211346Sodium hydrosulfide hydrateHCID 59680049HCID 59680049, compound

Product 1

HCID 59679904HCID 59679904, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

310 mg of 2-(3-nitrophenyl)thiazolo[5,4-c]pyridine (1.2 mmol) was mixed with 30 mL of MeOH along with 6 mL of water. Sodium hydrosulfide hydrate (6 eq, 7.24 mmol, 400 mg) was added and the reaction mixture was stirred under reflux for 3 hours. The reaction mixture was cooled to room temperature and concentrated. The aqueous layer was extracted with methylene chloride. The combined organic layers were dried (Na2SO4) and concentrated to afford 230 mg of 3-(thiazolo[5,4-c]pyridin-2-yl)benzenamine (84% crude yield) (MS, M++H=228).

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-67e650f5382e4e23a9b61d7e7a291a76
Source dataset
uspto-grants-2012_05
Patent number
US08178536B2

Reaction notes

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