Hydrochloric Acid → 6-(2-Chlorobenzoyl)-5-(2-chlorobenzoylamino)indan

HRID 36927Notes

Reaction equation

HRID 36927 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2)=[O:5].[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].[Sn](Cl)(Cl)(Cl)Cl.Cl>C(OCC)(=O)C>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([C:15]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][C:7]=1[NH:6][C:4](=[O:5])[C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[Cl:1])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 691102-Chlorobenzoyl chlorideHCID 7699162-chloro-N-(2,3-dihydro-1H-inden-5-yl)benzamide

Product 1

HCID 199365836-(2-Chlorobenzoyl)-5-(2-chlorobenzoylamino)indanYield 66.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-(2-chlorobenzoylamino)indan (16 g), 2-chlorobenzoyl chloride (15.5 g) and tin tetrachloride (10.2 ml) was heated at 130° C. for 30 minutes and, then, diluted with ethyl acetate (150 ml), followed by addition of 3N HCl (150 ml). The organic layer was separated and washed with water, 2N NaOH and water in the order mentioned and the solvent was distilled off. The residue was chromatographed on silica gel and eluted with hexane-acetone (4:1) to give 6-(2-chlorobenzoyl)-5-(2-chlorobenzoylamino)indan as oil (16.0 g, 66.2%).

Workup

  1. customThe organic layer was separated
  2. washwashed with water, 2N NaOH and water in the order
  3. distillationthe solvent was distilled off
  4. customThe residue was chromatographed on silica gel
  5. washeluted with hexane-acetone (4:1)

Sources & evidence

ORD record
ord-c3b85288842e4748a11fb74cde879943
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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