Pyridine → HCID 23130497, compound

HRID 2080098Notes

Reaction equation

HRID 2080098 reaction equation
[CH2:1]([O:8][C:9]1[S:13][C:12]([CH:14]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]1C=CC=CC=1.Cl.NO.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[S:13][C:12]([C:14]#[N:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 231306955-Benzyloxy-thiophene-2-carbaldehyde

Product 1

HCID 23130497HCID 23130497, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The resulting 5-benzyloxy-thiophene-2-carbaldehyde (171 mg) was dissolved in N,N-dimethylformamide (4 mL), pyridine (82 μl, 1.02 mmol) and hydroxylamine hydrochloride (65 mg, 0.94 mmol) were added thereto, followed by stirring for 30 minutes at 60° C., then, cooled on an ice bath. 1,1′-Carbonyldiimidazole (635 mg, 3.92 mmol) was added, the solution was warmed again to 60° C. and stirred for 35 minutes, triethylamine (272 μl, 1.96 mmol) was added, and the solution was further stirred for 30 minutes. The reaction mixture was cooled to room temperature, water was added, and the solution was extracted with ethyl acetate. The organic layer was sequentially washed with an aqueous solution of oxalic acid, an aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (30 mg, 0.14 mmol, 14%) was obtained.

Workup

  1. temperaturecooled on an ice bath
  2. temperaturethe solution was warmed again to 60° C.
  3. stirringstirred for 35 minutes
  4. stirringthe solution was further stirred for 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe organic layer was sequentially washed with an aqueous solution of oxalic acid
  8. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-fedfc1abb2b4489f9919741eb1e5ed6a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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