Hydrochloric Acid → 2-Acetylphenoxathiin

HRID 2398771Notes

Reaction equation

HRID 2398771 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:17])[CH3:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S.O>[C:15]([C:10]1[CH:9]=[CH:8][C:7]2[O:6][C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[S:13][C:12]=2[CH:11]=1)(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 9217PhenoxathiinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5151742-Acetylphenoxathiin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

Phenoxathiin (22.9 g) and acetyl chloride (8.8 ml) were dissolved in carbon disulphide (120 ml) and mechanically stirred while aluminum chloride (15.5 g) was added in small portions. The red mixture was stirred for 2 hr. at room temperature, then boiled under reflux on the water bath for a further 221/4 hr. The mixture was cooled and poured on to ice and hydrochloric acid, and the precipitated product filtered off, washed with water, and recrystallised once from ethanol and twice from petroleum ether (b.p. 80°-100° C.) to give the product m.p. 112° C.

Workup

  1. additionwas added in small portions
  2. customat room temperature
  3. temperatureThe mixture was cooled
  4. filtrationthe precipitated product filtered off
  5. washwashed with water
  6. customrecrystallised once from ethanol and twice from petroleum ether (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-95376986b3b546b28fde42948491b6ee
Source dataset
uspto-grants-1977_05
Patent number
US04025635

Reaction notes

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