Trichloroacetyl isocyanate → HCID 20233204, compound

HRID 65491Notes

Reaction equation

HRID 65491 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[C:3]([N:5]=[C:6]=O)=[O:4].[O:10]=[C:11]1[C:16]2[CH:17]=[C:18]3[C:23](=[C:24]([CH2:25][CH2:26][CH3:27])[C:15]=2[O:14][C:13]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:12]1)[NH:22][C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:20]C3=O>ClCCl>[CH3:31][O:30][C:28]([C:21]1[CH:20]=[C:6]([NH:5][C:3](=[O:4])[C:2]([Cl:9])([Cl:8])[Cl:1])[C:18]2[C:23](=[C:24]([CH2:25][CH2:26][CH3:27])[C:15]3[O:14][C:13]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:12][C:11](=[O:10])[C:16]=3[CH:17]=2)[N:22]=1)=[O:29]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 13101142Ethyl 6,9-dihydro-4,6-dioxo-8-methoxycarbonyl-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate

Product 1

HCID 20233204HCID 20233204, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloroacetyl isocyanate (1.18 ml, 10 mmol) was added to a solution of ethyl 6,9-dihydro-4,6-dioxo-8-methoxycarbonyl-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate (3.85 g, 10 mmol) in dichloromethane (20 ml) at room temperature. The solution was then agitated gently for 24 hours at room temperature and then the solvent removed by distillation in vacuo. Trituration of the resulting solid with ether gave the sub-title compound as yellow cubes, 4.25 g (80%), mp 167°-169° C.

Workup

  1. customthe solvent removed by distillation in vacuo

Sources & evidence

ORD record
ord-19465ca13e814e1fb1d4319d9cfaebfa
Source dataset
uspto-grants-1986_09
Patent number
US04614802

Reaction notes

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