Water → Methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate

HRID 931476

Reaktionsgleichung

Reaktionsgleichung von HRID 931476
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[C:19](=[S:22])([O-:21])[CH3:20].[K+].O>CC(C)=O.[I-].[K+]>[C:19]([S:22][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8])(=[O:21])[CH3:20]

Komponenten

6

Edukt 3

HCID 962WaterHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoateHCID 23670855Potassium ethanethioate

Produkt 1

HCID 86709133Methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoateAusbeute 104,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of methyl 4-[4-(chloromethyl)-5-methyl-1,3-oxazol-2-yl]benzoate (5 g, 18.82 mmol, 1.00 equiv), potassium ethanethioate (2.68 g, 23.47 mmol, 1.25 equiv) and potassium iodide (120 mg, 0.72 mmol, 0.04 equiv) in acetone (40 mL) was stirred at 35° C. for 30 min. Water (50 mL) was added to quench the reaction. The resulting solution was extracted with 3×100 mL of ethyl acetate. The combined organic layers was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 6.03 g of crude methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate as a white solid.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
  4. washThe combined organic layers was washed with 2×200 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6249d9fff76b4986b8b34bf8db18c312
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296732B2

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