Water → 5-Methyl-4,5-dihydro-thieno[2,3-c]-pyridine

HRID 1875345Notes

Reaction equation

HRID 1875345 reaction equation
C[CH:2](NC=O)[CH2:3][C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+].[C:20](#[N:22])[CH3:21]>>[CH3:2][CH:3]1[N:22]=[CH:20][C:21]2[S:5][CH:6]=[CH:7][C:8]=2[CH2:4]1

Participants

6

Reactant 5

HCID 962WaterHCID 6342Acetonitrile2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 64990444N-(1-Methyl-2-thiophen-2-yl-ethyl)-formamide

Product 1

HCID 574239795-Methyl-4,5-dihydro-thieno[2,3-c]-pyridine

Procedure

A solution of 6.6 g (33.1 mmol) N-(1-methyl-2-thiphen-2-yl-ethyl)-formamide in 200 ml acetonitrile is cooled in the ice bath and slowly combined with a solution of 6.1 ml (66.3 mmol) phosphorus oxychloride in 50 ml acetonitrile. The mixture is first of all stirred for a further three hours in the ice bath and then for 16 hours at RT. Then it is poured onto 200 ml of water, made alkaline with 9 g of solid sodium hydroxide and extracted three times with ethyl acetate. The combined organic phases are combined with activated charcoal and sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. extractionextracted three times with ethyl acetate
  2. filtrationfiltered
  3. customevaporated down i

Sources & evidence

ORD record
ord-9171460501aa452c84596765865f955f
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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