2-Furancarbonyl chloride → HCID 9904767, compound

HRID 1196915Notes

Reaction equation

HRID 1196915 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=[O:15].[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21](Cl)=[O:22]>CN(C)C=O.CN(C)C1C=CN=CC=1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([C:21]([C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)=[O:22])[C:7]1=[O:15]

Participants

5

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 14819388HCID 14819388, compound

Product 1

HCID 9904767HCID 9904767, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-(2-thiazolyl)-2-oxindole (0.6 g, 2.7 mM) in dimethylformamide (8 ml) at 0° C. was added 4-dimethylaminopyridine (0.847 g, 2.2 eq.) and the mixture stirred for 5 minutes. Then, a solution of 2-furoyl chloride (0.31 ml, 3.04 mM, 1.1 eq.) in dimethylformamide (2 ml) was added dropwise and the mixture stirred for 15 minutes at 0° C. and then at room temperature for 2 hours. The reaction was poured onto about 100 ml of ice/2N HCl, and the resulting yellow precipitate recovered by filtration, washed with water and air-dried. Recrystallization from toluene-hexane (1:1) afforded 0.585 g (64%) of title product as yellow needles; m.p. 156°-157° C.

Workup

  1. stirringthe mixture stirred for 15 minutes at 0° C.
  2. waitat room temperature for 2 hours
  3. filtrationthe resulting yellow precipitate recovered by filtration
  4. washwashed with water
  5. customair-dried
  6. customRecrystallization from toluene-hexane (1:1)

Sources & evidence

ORD record
ord-6a1dd14a69a54a79a36dd0e72bfb65e8
Source dataset
uspto-grants-1992_05
Patent number
US05116854

Reaction notes

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