Potassium Carbonate → HCID 1533737, compound

HRID 1763019Notes

Reaction equation

HRID 1763019 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.S(C)C>[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

5

Reactant 2

HCID 11430Potassium CarbonateHCID 13756049HCID 13756049, compound

Product 1

HCID 1533737HCID 1533737, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 200ml 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 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. extractionThe MeOh extract
  5. customwas evaporated
  6. customthe residue was chromatographed on silica gel
  7. customthe purified product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-ce6592c4bb7e4c1f9904beeb5f8b5f2d
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

Loading…