9-Acridinecarbonyl chloride → HCID 15895750, compound

HRID 565130Notes

Reaction equation

HRID 565130 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15](Cl)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[S:18]([O:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:37][C:34]2[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][O:28][S:18]([C:21]4[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=4)(=[O:19])=[O:20])=[CH:36][CH:35]=2)=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6099609-Acridinecarbonyl chlorideHCID 11460554HCID 11460554, compound

Product 1

HCID 15895750HCID 15895750, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 30 ml of pyridine, 2.4 g of the compound (2) obtained in Example 2 were dissolved. Under ice cooling and stirring, 2.9 g of the compound (1) obtained in Example 1 were added in small portions. Subsequent to stirring at room temperature for 2 hours, the pyridine was distilled off under reduced pressure. CHCl3 was added further, and distillation was repeated twice under reduced pressure. The residue was isolated and purified by chromatography on a silica gel column (eluent: CHCl3), whereby 2.7 g of the compound (3) were obtained (yield: 54%).

Workup

  1. stirringSubsequent to stirring at room temperature for 2 hours
  2. distillationthe pyridine was distilled off under reduced pressure
  3. additionCHCl3 was added further
  4. distillationdistillation
  5. customThe residue was isolated
  6. custompurified by chromatography on a silica gel column (eluent: CHCl3)

Sources & evidence

ORD record
ord-1287d806aec74e58a380eba92b1d5c05
Source dataset
uspto-grants-2001_01
Patent number
US06171520B2

Reaction notes

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