Pyridine → HCID 3769639, compound

HRID 374521Notes

Reaction equation

HRID 374521 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1.[Cl:20][C:21]1[C:22]2[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=2[S:24][C:25]=1[C:26]([NH2:28])=O>C(Cl)Cl.O>[Cl:20][C:21]1[C:22]2[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=2[S:24][C:25]=1[C:26]#[N:28]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 6070523-Chlorobenzo(b)thiophene-2-carboxamide

Product 1

HCID 3769639HCID 3769639, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (11.90 g, 56.6 mmol) is added dropwise to a mixture of pyridine (5.23 g, 66.1 mmol) and 3-chlorobenzo[b]thiophene-2-carboxamide (10.00 g, 47.2 mmol) in methylene chloride at 0° C. The reaction mixture is warmed to room temperature over one hour, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water, one molar hydrochloric acid and brine, dried over MgSO4 and concentrated in vacuo to obtain a yellow solid. The solid is recrystallized from ethyl acetate and hexane to give the title product as off-white needles (8.80 g, 96%).

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts are washed sequentially with water, one molar hydrochloric acid and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow solid
  6. customThe solid is recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-1198b791c6a94a2d808eb777777a1cda
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Reaction notes

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