HCID 22466634, compound → HCID 22466702, compound

HRID 1935092Notes

Reaction equation

HRID 1935092 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]#[N:25])[CH:6]=[CH:7][CH:8]=1.[C:26]([O-:29])(=[S:28])[CH3:27].[K+]>CN(C=O)C>[C:26]([S:28][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]#[N:25])[CH:6]=[CH:7][CH:8]=1)(=[O:29])[CH3:27]

Participants

4

Reactant 2

HCID 22466634HCID 22466634, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 22466702HCID 22466702, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[3-(chloromethyl)phenylamino]-6,7-dimethoxy-3-quinolinecarbonitrile (0.97 g, 2.7 mmol) in 5.4 ml of DMF was added potassium thioacetate (0.93 g, 8.1 mmol) at 25° C. After 30 m the mixture was partitioned with methylene chloride and water. The organic layer was washed with water, dried, and concentrated. The residue was recrystallized from ethyl acetate to give 0.43 g of yellow solid, mp 172-177° C.

Workup

  1. customAfter 30 m the mixture was partitioned with methylene chloride and water
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-585b67ed292b46a597abd70563e4ca99
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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