Methanol → 1-Chloro-7-hydroxy-4-nitro-9H-thioxanthen-9-one

HRID 1380621Notes

Reaction equation

HRID 1380621 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.B(Br)(Br)Br.CO>C(Cl)Cl>[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

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide3×HCID 13590116HCID 13590116, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The requisite 1-chloro-7-hydroxy-4-nitrothioxanthone was prepared as follows: To a suspension of 5.0 g of 1-chloro-7-methoxy-4-nitro-thioxanthone in 50 ml of methylene chloride was added 20 ml of boron tribromide in methylene chloride (1M). The mixture was stirred for two days, and an additional 20 ml of boron tribromide was added. The mixture was stirred for three hours at room temperature and heated under reflux for two hours. An additional 20 ml of boron tribromide was added and the mix was heated under reflux for two hours. The mixture was cooled in an ice bath and 50 ml of methanol was added carefully. The solution was heated under reflux for one hour, and the solvent was removed in vacuo. The residue was boiled in about 50 ml of ethanol, collected, and retreated with hot ethanol to provide the product as an orange powder, mp 240°-254° (dec).

Workup

  1. stirringThe mixture was stirred for three hours at room temperature
  2. temperatureheated
  3. temperatureunder reflux for two hours
  4. temperaturethe mix was heated
  5. temperatureunder reflux for two hours
  6. temperatureThe mixture was cooled in an ice bath
  7. temperatureThe solution was heated
  8. temperatureunder reflux for one hour
  9. customthe solvent was removed in vacuo
  10. customcollected

Sources & evidence

ORD record
ord-4cfaf137b9ba456db60c66cd75be975f
Source dataset
uspto-grants-1986_04
Patent number
US04582851

Reaction notes

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