p-Toluenesulfonyl isocyanate → HCID 13352258, compound

HRID 2417928Notes

Reaction equation

HRID 2417928 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([CH2:16][CH2:17][CH3:18])[C:6]=2[O:5][C:4]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:3]1)[NH:13][C:12]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][C:10]3=O.[C:29]1([CH3:41])[CH:34]=[CH:33][C:32]([S:35]([N:38]=C=O)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClC(Cl)C>[CH3:22][O:21][C:19]([C:12]1[CH:11]=[C:10]([NH:38][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:41])=[CH:30][CH:31]=2)(=[O:36])=[O:37])[C:9]2[C:14](=[C:15]([CH2:16][CH2:17][CH3:18])[C:6]3[O:5][C:4]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:3][C:2](=[O:1])[C:7]=3[CH:8]=2)[N:13]=1)=[O:20]

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 13101142Ethyl 6,9-dihydro-4,6-dioxo-8-methoxycarbonyl-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate

Product 1

HCID 13352258HCID 13352258, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Ethyl 6,9-dihydro-4,6-dioxo-8-methoxycarbonyl-10-propyl-4Hpyrano[3,2-g]quinoline-2-carboxylate (38.5 g, 0.1 mol) was suspended in dichloroethane (200 ml) and 4-toluene-sulphonyl isocyanate (15.1 ml; 0.1 mol) added at room temperature. The whole was then refluxed for 16 hours, allowed to cool, and filtered, to give the sub-title compound as brillant yellow cubes, 44.0 g (82%), m.p. 219° C.

Workup

  1. temperatureThe whole was then refluxed for 16 hours
  2. temperatureto cool
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b1f9e41e2dd44a929a54b3d9c53f4c28
Source dataset
uspto-grants-1984_09
Patent number
US04471119

Reaction notes

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