Methanol → HCID 59679904, compound

HRID 2264993Notes

Reaction equation

HRID 2264993 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-fd59413f04784b2fb4f761533d554107
Source dataset
uspto-grants-2010_12
Patent number
US07855289B2

Reaction notes

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