Dichloromethane → HCID 178466992, compound

HRID 2292625Notes

Reaction equation

HRID 2292625 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:15])[CH3:14])[NH:7]2.[C:17]1([S:23]([N:26]=C=O)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:26][S:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:25])=[O:24])[CH:5]=[C:6]([C:13](=[O:15])[CH3:14])[NH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 76096Phenylsulphonyl isocyanateHCID 21478939HCID 21478939, compound

Product 1

HCID 178466992HCID 178466992, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 5,7-dichloro-2-acetyl-1,4-dihydroquinol-4-one (0.28 g, 1.1 mmol) and benzenesulfonyl isocyanate (0.16 mL, 1.2 mmol) in acetonitrile (5 mL). Heat at reflux for 3 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, 163°-164° C. Rf =0.32 TLC/silica gel/dichloromethane. Elem. Anal. Calcd. for C17H12Cl2 N2O3S: C, 51.65; H, 3.04; N, 7.09.

Workup

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

Sources & evidence

ORD record
ord-f17f2af33b7040a4872e924488c841d8
Source dataset
uspto-grants-1997_11
Patent number
US05684017

Reaction notes

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