Water → HCID 86759277, compound

HRID 431093Notes

Reaction equation

HRID 431093 reaction equation
[CH:1](/[C:9]1[C:10]([OH:31])=[C:11]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18](/[CH:22]=[CH:23]\[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]=2[OH:30])[CH:12]=[CH:13][CH:14]=1)=[CH:2]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1[CH:37]=[CH:36]C=CC=1.[C:38](OC(=O)C)(=[O:40])[CH3:39].[OH2:45]>C(Cl)(Cl)Cl>[CH:22](/[C:18]1[C:17]([O:30][C:36](=[O:45])[CH3:37])=[C:16]([S:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9](/[CH:1]=[CH:2]\[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]=2[O:31][C:38](=[O:40])[CH3:39])[CH:21]=[CH:20][CH:19]=1)=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86759278HCID 86759278, compound

Product 1

HCID 86759277HCID 86759277, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
22 °C

Procedure

To a reaction mixture containing the (Z)-styryl 2-hydroxyphenylsulfide (5 mmol), anhydrous pyridine (5 mmol) and acetic anhydride (5 mmol) in dry chloroform (10 ml) is stirred for 5 hours at room temperature (22° C.). The reaction mixture is then diluted with water (20 ml) and shaken well in a separating funnel. The lower organic layer is collected and dried over anhydrous sodium sulfate. Evaporation of the chloroform in vacuum yields the corresponding (Z)-styryl 2-acetoxyphenylsulfide (I) as an oil, or in most cases a colorless solid. The products are purified by TLC or by fractional crystallization.

Workup

  1. stirringshaken well in a separating funnel
  2. customThe lower organic layer is collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the chloroform in vacuum

Sources & evidence

ORD record
ord-39ffca204c614dd78144203a1ff38717
Source dataset
uspto-grants-2003_12
Patent number
US06656968B1

Reaction notes

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