Thionyl Chloride → HCID 13590116, compound

HRID 1380619Notes

Reaction equation

HRID 1380619 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]([S:8][C:9]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:7]=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:11](=[O:13])[C:10]3[C:9](=[CH:17][CH:16]=[C:15]([O:18][CH3:19])[CH:14]=3)[S:8][C:6]=2[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13590115HCID 13590115, compound

Product 1

HCID 13590116HCID 13590116, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The requisite 1-chloro-7-methoxy-4-nitrothioxanthone was prepared as follows: A mixture of 118.5 g (0.35 mole) of 2-(5-chloro-2-nitrophenylthio)-5-methoxybenzoic acid and 131 ml of thionyl chloride in 600 ml of toluene was heated under reflux for 1.5 hours. The mixture was concentrated in vacuo, and the resulting solid was dissolved in 950 ml of nitrobenzene with heating and then cooled to 0° in an ice bath. Aluminum chloride (44.2 g) was added in portions over 0.5 hour with cooling, and the mixture was then allowed to come to room temperature and stirred overnight. The mixture was poured into 5 l of cold water. As much of the water layer as possible was decanted. The residue was triturated twice with 1 l portions of methanol and then twice with 2 l portions of methanol. The oil was triturated with 4 l of methanol and a solid resulted. This was washed with methanol and dried in vacuo at 75° to give 72.7 g of the product as a brownish-yellow solid, mp 235°-240°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe resulting solid was dissolved in 950 ml of nitrobenzene
  5. temperaturewith heating
  6. temperaturecooled to 0° in an ice bath
  7. additionAluminum chloride (44.2 g) was added in portions over 0.5 hour
  8. temperaturewith cooling
  9. customto come to room temperature
  10. additionThe mixture was poured into 5 l of cold water
  11. customAs much of the water layer as possible was decanted
  12. customThe residue was triturated twice with 1 l portions of methanol
  13. customThe oil was triturated with 4 l of methanol
  14. customa solid resulted
  15. washThis was washed with methanol
  16. customdried in vacuo at 75°

Sources & evidence

ORD record
ord-1ea219a371d1490697739f40e4252ecc
Source dataset
uspto-grants-1986_04
Patent number
US04582851

Reaction notes

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