Ammonia → Thieno(3,2-c)pyridine

HRID 971902Notes

Reaction equation

HRID 971902 reaction equation
C([CH:4]1[N:9](N=O)[CH2:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[CH:5]1O)(O)=O.FC(F)(F)C(O)=O.N>>[S:14]1[C:6]2[CH:5]=[CH:4][N:9]=[CH:8][C:7]=2[CH:12]=[CH:13]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 21312555HCID 21312555, compound

Product 1

HCID 67500Thieno(3,2-c)pyridineYield 56%

Procedure

11.4 g of the derivative of the formula (IV) of Example 2 is added portionwise to 55 cc trifluoroacetic acid stirred at room temperature. The temperature rises from 19° C. to 24° C., and russet fumes are evolved. The material is allowed to cool to room temperature; the reaction mixture is then poured over ice, made basic by addition of concentrated aqueous ammonia and extracted with diisopropyl ether. The organic extracts are washed with water, dried over sodium sulfate and evaporated to dryness. Distillation in vacuo of the residue gives 3.8 g (Yield: 56%) thieno[3,2-c]pyridine.

Workup

  1. customrises from 19° C. to 24° C.
  2. temperatureto cool to room temperature
  3. additionthe reaction mixture is then poured over ice
  4. extractionextracted with diisopropyl ether
  5. washThe organic extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. distillationDistillation in vacuo of the residue

Sources & evidence

ORD record
ord-f1422ed40925488d9459c239c30ac894
Source dataset
uspto-grants-1979_07
Patent number
US04161599

Reaction notes

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