Acetic Anhydride → 2-Methyl-[1,3]thiazolo[4,5-c]pyridine

HRID 1253220Notes

Reaction equation

HRID 1253220 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[SH:10])([O-])=O.[C:11](OC(=O)C)(=O)[CH3:12]>C(O)(=O)C.[Zn]>[CH3:11][C:12]1[S:10][C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:1]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178526807HCID 178526807, compound

Product 1

HCID 6407212-Methyl-[1,3]thiazolo[4,5-c]pyridineYield 44.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.3 g of 3-nitropyridine-4-thiol in 4 ml of acetic acid and 15 ml of acetic anhydride containing 1.5 g of zinc dust was heated at reflux for four hours. The reaction mixture was cooled and concentrated to an oil. The oil was dissolved in 5N sodium hydroxide and the alkaline solution was extracted with diethyl ether. The extracts were combined, dried and concentrated to dryness to afford 557 mg of 2-methylthiazolo[4,5-c]pyridine. M+Theory 150; Found 150.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for four hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated to an oil
  5. dissolutionThe oil was dissolved in 5N sodium hydroxide
  6. extractionthe alkaline solution was extracted with diethyl ether
  7. customdried
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b2b877af11624f7986d13499d71bdd0c
Source dataset
uspto-grants-1988_05
Patent number
US04748172

Reaction notes

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