Phenylsulphonyl isocyanate → HCID 178450748, compound

HRID 1378335Notes

Reaction equation

HRID 1378335 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(#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][CH2:11][CH2:2][CH2:3][CH3:4])=[O:14])[NH:7]2

Participants

4

Reactant 2

HCID 76096Phenylsulphonyl isocyanateHCID 131720193HCID 131720193, compound

Product 1

HCID 178450748HCID 178450748, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 5,7-dichloro-quinolin-4-one-2-carboxylic acid, butyl ester (1.00 g, 3.2 mmol) and benzenesulfonyl isocyanate (0.85 mL, 6.3 mmol) in acetonitrile (15 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 ethyl acetate/hexane to give the title compound as a solid: TLC Rf =0.38 (silica gel, 2% acetone/dichloromethane); mp; 94°-95° C. Elem. Anal. calculated for C20H18Cl2N2O4S: C, 52.98; H, 4.00; N, 6.18. Found: C, 53.27; H, 3.95; N, 6.12.

Workup

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

Sources & evidence

ORD record
ord-824751a6ce5c4d379e2c4694bac317b9
Source dataset
uspto-grants-1997_09
Patent number
US05668143

Reaction notes

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