Thionyl Chloride → HCID 19592582, compound

HRID 613494Notes

Reaction equation

HRID 613494 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH2:15][CH3:16])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:17][C:18](=[O:27])[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])(=O)[NH2:2].S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH2:15][CH3:16])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:17][C:18](=[O:27])[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])#[N:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 19593050HCID 19593050, compound

Product 1

HCID 19592582HCID 19592582, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-carbamoyl-8-(2,6-dichlorobenzoylamino)-4-ethoxyquinoline (122 mg) in dimethylformamide was added thionyl chloride (53.9 mg), and the mixture was stirred for 30 minutes at ambient temperature. The mixture was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 3-cyano-8-(2,6-dichlorobenzoylamino)-4-ethoxyquinoline (89.9 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-0baedb797f4e4045b00707a46d84ac38
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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