Triethylamine → HCID 15307969, compound

HRID 2293227Notes

Reaction equation

HRID 2293227 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].C(N(CC)CC)C.[NH2:17][C:18]1[CH:39]=[CH:38][C:21]([C:22]([N:24]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=3)=[O:23])=[CH:20][CH:19]=1>ClCCl>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([N:24]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=3)=[O:23])=[CH:38][CH:39]=1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27376053-Methyl-2-thenoyl ChlorideHCID 15410466HCID 15410466, compound

Product 1

HCID 15307969HCID 15307969, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.193 g (1.2 mmol) of 3-methylthiophene-2-carbonyl chloride in 3 ml of dichloromethane, cooled to 0° C., is added 209 μl triethylamine. The mixture is stirred and 0.30 g (1 mmol) of 5-(4-aminobenzoyl)-5,6-dihydrophenanthridine is added. The mixture is stirred at room temperature overnight and then concentrated under vacuum. To the residue is added 30 ml of ethyl acetate and the mixture washed with 2 ml each of water, 2N citric acid, 1M sodium bicarbonate and brine. The organic layer is dried (Na2SO4) and the solvent removed to give 0.30 g of solid. The solid is chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as solvent to give 150 mg of product as a yellow foam.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. concentrationconcentrated under vacuum
  3. additionTo the residue is added 30 ml of ethyl acetate
  4. washthe mixture washed with 2 ml each of water, 2N citric acid, 1M sodium bicarbonate and brine
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-bc2f243a65d547fb838f728be5d35a70
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

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