2-Thiophenecarbonyl chloride → HCID 18973068, compound

HRID 2394373Notes

Reaction equation

HRID 2394373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[C:6](=[O:13])[CH2:5]2.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](Cl)=[O:20]>CN(C)C1C=CN=CC=1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[C:6](=[O:13])[CH:5]2[C:19](=[O:20])[C:15]1[S:14][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 18973025HCID 18973025, compound

Product 1

HCID 18973068HCID 18973068, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1-ethyl-7-azaoxindole (400 mg, 2.03 mmol) and 4-dimethylaminopyridine (537 mg, 4.4 mmol) in DMF (10 mL) at 0° C. was added thiophene-2-carbonyl chloride (0.24 mL, 2.24 mmol). The reaction mixture was stirred at room temperature for 2 hours and then poured into ice/water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried (magnesium sulfate) and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with chloroform. Fractions containing only the desired product were combined and concentrated to afford the title compound as a solid which was recrystallized from hexanes. The yield of recrystallized material was 29 mg (50%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel eluting with chloroform
  6. additionFractions containing only the desired product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b4fa863a1e2445b79ae0c25ac7dacf81
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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