Pyridine → 4-Acetyloxy-1-chlorothioxanthone

HRID 36396Notes

Reaction equation

HRID 36396 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.C[O:19][C:20]1C2C(=O)C3C(=CC=CC=3)SC=2C(OC)=C[CH:21]=1.N1C=CC=CC=1.C(Cl)(=O)C>CC(C)=O>[C:20]([O:17][C:5]1[C:6]2[S:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14](=[O:16])[C:15]=2[C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:19])[CH3:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 28259241-Chloro-4-hydroxythioxanthoneHCID 125538111,4-Dimethoxythioxanthone

Product 1

HCID 199386334-Acetyloxy-1-chlorothioxanthone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Chloro-4-hydroxythioxanthone as prepared in Example 1 (13.1 g) and pyridine (1O g) was stirred in acetone (50 ml) at 50°. Acetyl chloride (4.3 g) was added over 0.25 h and the mixture stirred and heated under reflux for a further hour. The mixture was cooled to 20° and quenched with water (150 ml). The resulting solution was extracted with chloroform (50 ml), separated and the organic phase washed twice with water. The organic phase was evaporated to dryness under reduced pressure and the residue crystallised from methanol with a carbon treatment to afford the title compound, 4.1 g (27.0%) as a pale yellow solid of mp 141°-42°. Analysis C15H9ClO3S=304.745 Requires C 59.11% H 2.98% Cl 11.63% S 10.52% Found C 59.10% H 3.06% Cl 11.59% S 10.41%

Workup

  1. temperatureheated
  2. temperatureunder reflux for a further hour
  3. temperatureThe mixture was cooled to 20°
  4. customquenched with water (150 ml)
  5. extractionThe resulting solution was extracted with chloroform (50 ml)
  6. customseparated
  7. washthe organic phase washed twice with water
  8. customThe organic phase was evaporated to dryness under reduced pressure
  9. customthe residue crystallised from methanol with a carbon treatment

Sources & evidence

ORD record
ord-8deba499fd3748e58bacc2e424f7a0df
Source dataset
uspto-grants-1995_05
Patent number
US05414092

Reaction notes

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