2-Thiophenecarbonyl chloride → HCID 13957979, compound

HRID 1382800Notes

Reaction equation

HRID 1382800 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:13])[CH3:12])[C:6](=[O:14])[CH2:5]2.[C:15]1([C:20](Cl)=[O:21])[S:19][CH:18]=[CH:17][CH:16]=1>CN(C1C=CN=CC=1)C.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:13])[CH3:12])[C:6](=[O:14])[CH:5]2[C:20](=[O:21])[C:15]1[S:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 13958009HCID 13958009, compound

Product 1

HCID 13957979HCID 13957979, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 0.75 g (3.6 mmole) of 5-chloro-1-acetyl-2-oxindole and 0.96 ml (7.9 mmole) of 4-(N,N-dimethylamino)pyridine in 20 ml of N,N-dimethylformamide, cooled to ca. 0° C, was added a solution of 0.4 ml (3.7 mmole) of 2-thenoyl chloride in 5 ml of N,N-dimethylformamide, dropwise, during a few minutes. The reaction mixture was stirred for 30 minutes at ca. 0° C. and then for 3.5 hours at room temperature, and then it was poured into 500 ml of ice-cold 2N hydrochloric acid. The resulting solution was extracted with ethyl acetate, and the extracts were washed with water, followed by saturated sodium chloride solution, and then they were dried using magnesium sulfate. Evaporation of the dried ethyl acetate solution gave 1.1 g of crude product. The latter was purified by column chromatography using silica gel and eluting with dichloromethane-ethyl acetate mixtures, followed by recrystallization from a small volume of toluene, to give 250 mg of the title compound, m.p. 168°-170° C.

Workup

  1. waitdropwise, during a few minutes
  2. waitfor 3.5 hours at room temperature
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. washthe extracts were washed with water
  5. customthey were dried
  6. customEvaporation of the dried ethyl acetate solution
  7. customgave 1.1 g of crude product
  8. customThe latter was purified by column chromatography
  9. washeluting with dichloromethane-ethyl acetate mixtures
  10. customfollowed by recrystallization from a small volume of toluene

Sources & evidence

ORD record
ord-9fffaef58b9a4741a2a74db8ab78bd41
Source dataset
uspto-grants-1989_02
Patent number
US04808601

Reaction notes

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