Phenothiazine → Ethylene Oxide

HRID 2231925Notes

Reaction equation

HRID 2231925 reaction equation
[CH:1]1[C:14]2NC3C(=CC=CC=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(S[CH:22]([OH:24])[CH3:23])C=CC=CC=1>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[C:5]1([SH:6])[CH:14]=[CH:1][CH:2]=[CH:3][CH:4]=1.[CH2:22]1[O:24][CH2:23]1

Participants

6

Reactant 2

HCID 7108Phenothiazine2×HCID 21400465HCID 21400465, compound

Product 2

HCID 6354Ethylene OxideHCID 7969Thiophenol

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent2×

Procedure

One mole of phenothiazine is placed in a one liter, round bottom flask with 300 ml of toluene. The reaction is maintained under a nitrogen blanket. To the mixture of the phenothiazine and toluene is added 0.05 mole of sulfuric acid as a catalyst. The mixture is then heated to reflux temperature and 1.1 moles of phenylthioethanol is added dropwise over a period of approximately 90 minutes. The phenylthiothethanol is obtained from the reaction of thiophenol and ethylene oxide with a basic catalyst. Water is continuously removed as it is formed in the reaction process.

Workup

  1. temperatureThe reaction is maintained under a nitrogen blanket
  2. temperatureThe mixture is then heated
  3. additionis added dropwise over a period of approximately 90 minutes

Sources & evidence

ORD record
ord-35606582345c4f8591f3b300768d94b8
Source dataset
uspto-grants-1988_11
Patent number
US04785095

Reaction notes

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