Hydrochloric Acid → HCID 18969593, compound

HRID 399037Notes

Reaction equation

HRID 399037 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH:11]2OCCO2)=[CH:4][CH:3]=1.Cl.C([O-])(=O)C.[NH4+:29]>CC(C)=O.O.C(OCC)(=O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:29][CH:11]=[CH:10][C:9]=2[S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 18969598HCID 18969598, compound

Product 1

HCID 18969593HCID 18969593, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 4'-chloro-3-(1,3-dioxolan-2-yl)-2-(phenylthio)propiophenone (0.87 g, 2.5 mmol) and 4N hydrochloric acid (15 mL) in acetone is stirred at 45° C. for 3 hours, cooled, and diluted with water and ethyl acetate. The organic phase is separated, washed with 5% sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. A solution of the residue in acetic acid is treated with ammonium acetate (3.0 g, 0.039 mol), stirred at 45° C. for 20 minutes, cooled to room temperature, and diluted with water and ethyl acetate. The organic phase is separated, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a dark residue. Flash column chromatography of the dark residue using silica gel and a 1:1 ethyl acetate/hexanes solution gives the title product as a dark brown syrup which is identified by NMR spectral analyses.

Workup

  1. temperaturecooled
  2. customThe organic phase is separated
  3. washwashed with 5% sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue
  7. temperaturecooled to room temperature
  8. customThe organic phase is separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto obtain a dark residue

Sources & evidence

ORD record
ord-d55d5ab1a53149ff9b38a56cf0285341
Source dataset
uspto-grants-1998_10
Patent number
US05817691

Reaction notes

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