Potassium Carbonate → HCID 1533737, compound

HRID 1249416Notes

Reaction equation

HRID 1249416 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([NH:11][C:12]2[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH:13]=2)[CH:4]=1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[NH2:8][C:7]1[C:6]2[C:5]([N:11]=[C:12]3[C:13]=1[C:14](=[O:18])[CH2:15][CH2:16][CH2:17]3)=[CH:4][C:3]([Cl:2])=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13756049HCID 13756049, compound

Product 1

HCID 1533737HCID 1533737, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 200 ml of tetrahydrofuran were combined 5.00 g of 4-chloro-2-(3-oxocyclohexen-1-yl)aminobenzonitrile hydrochloride, 4.88 g (2 eq) milled anhydrous K2CO3, and 0.36 g (0.1 eq) of CuBr (CH3)2S used as a catalyst. The mechanically stirred mixture was refluxed overnight. It was then evaporated to a residue and extracted with several portions of MeOH. The insoluble inorganics were dissolved in water to remove any product not extracted by the MeOH, but none were detected. The MeOH extract was evaporated and the residue was chromatographed on silica gel and then the purified product was recrystallized from EtOAc to yield 2.07 g (47%) of a solid, melting point 285°-287° C.

Workup

  1. temperatureThe mechanically stirred mixture was refluxed overnight
  2. customIt was then evaporated to a residue
  3. extractionextracted with several portions of MeOH
  4. dissolutionThe insoluble inorganics were dissolved in water
  5. customto remove any product not
  6. extractionextracted by the MeOH, but none
  7. extractionThe MeOH extract
  8. customwas evaporated
  9. customthe residue was chromatographed on silica gel
  10. customthe purified product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-9ad16eaae18e4879a0c7b12f92dcd441
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Reaction notes

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