Acetonitrile → HCID 178469282, compound

HRID 1378334Notes

Reaction equation

HRID 1378334 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=O)[CH2:5][C:6]([C:13]([OH:15])=[O:14])=[N: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.[C:29](#N)[CH3:30]>>[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][CH2:29][CH3:30])=[O:14])[NH:7]2

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 76096Phenylsulphonyl isocyanateHCID 131720193HCID 131720193, compound

Product 1

HCID 178469282HCID 178469282, compound

Procedure

Combine 5,7-dichloro-quinolin-4-one-2-carboxylic acid, ethyl ester (0.59 g, 2.1 mmol) and benzenesulfonyl isocyanate (0.56 mL, 4.2 mmol) in acetonitrile (10 mL). Heat to reflux under an inert atmosphere. After 16 hours, quench with methanol (5 mL). Evaporate in vacuo. Chromatograph on silica gel eluting with 2% acetone/dichloromethane. Recrystallize from acetonitrile to give the title compound as a solid: TLC Rf =0.31 (silica gel, 2% acetone/dichloromethane); mp; 184°-185° C. Elem. Anal. calculated for C18H14Cl2N2O4S: C, 50.83; H, 3.32; N, 6.59. Found: C, 51.04; H, 3.33; N, 6.56.

Workup

  1. temperatureHeat
  2. temperatureto reflux under an inert atmosphere
  3. customquench with methanol (5 mL)
  4. customEvaporate in vacuo
  5. customRecrystallize from acetonitrile

Sources & evidence

ORD record
ord-407f8f56f56a448c8c122f49aa308cba
Source dataset
uspto-grants-1997_09
Patent number
US05668143

Reaction notes

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