Aluminum(III) Chloride → 1-Chloro-7-hydroxy-4-nitro-9H-thioxanthen-9-one

HRID 364209Notes

Reaction equation

HRID 364209 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:17]C)[CH:12]=3)[S:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:17])[CH:12]=3)[S:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 13590116HCID 13590116, compound

Product 1

HCID 135901181-Chloro-7-hydroxy-4-nitro-9H-thioxanthen-9-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 25 g of 1-chloro-7-methoxy-4-nitro-9H-thioxanthen-9-one, 32.1 g of anhydrous aluminum chloride, and 300 ml of 1,2-dichloroethane is heated under reflux for 1.5 hours. The mixture is concentrated, then treated with 640 ml of concentrated HCl. After 1 hour, the slurry is filtered, and then washed with 500 ml of water followed by 300 ml of 2-propanol, to afford the title compound as a gold solid, mp>300° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe mixture is concentrated
  4. additiontreated with 640 ml of concentrated HCl
  5. filtrationthe slurry is filtered
  6. washwashed with 500 ml of water

Sources & evidence

ORD record
ord-51da5aa45f4143d6a249e4d919b938a9
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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