Dichloromethane → HCID 178519482, compound

HRID 2292624Notes

Reaction equation

HRID 2292624 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=O)[CH:5]=[C:6]([C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:7]2.[C:22]1([S:28]([N:31]=C=O)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.ClCCl>C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[N:31][S:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:30])=[O:29])[CH:5]=[C:6]([C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 76096Phenylsulphonyl isocyanateHCID 21478957HCID 21478957, compound

Product 1

HCID 178519482HCID 178519482, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 5,7-dichloro-2-benzoyl-1,4-dihydroquinolin-4-one (0.57 g, 1.8 mmol) and benzenesulfonyl isocyanate (0.26 mL, 2.0 mmol) in acetonitrile (9 mL) and heat at reflux for 18 hours. Add methanol (5 mL) to quench the reaction. Evaporate in vacuo to obtain a residue. Chromatograph the residue on a column of silica gel eluting with dichloromethane to obtain a solid. Recrystallize the solid from ethyl acetate/hexane to give the title compound; mp, 186°-187° C. Rf =0.37 TLC/silica gel/dichloromethane. Elem. Anal. Calcd. for C22H14Cl2 N2O3S: C, 57.77; H, 3.09; N, 6.13. Found: C, 57.76; H, 3.22; N, 5.91.

Workup

  1. temperatureat reflux for 18 hours
  2. customAdd methanol (5 mL) to quench
  3. customthe reaction
  4. customEvaporate in vacuo
  5. customto obtain a residue
  6. customRecrystallize the solid from ethyl acetate/hexane

Sources & evidence

ORD record
ord-23d0a8a96c144ee68794301005e19868
Source dataset
uspto-grants-1997_11
Patent number
US05684017

Reaction notes

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