4-Toluenesulfonyl chloride → (1-((4-Methylphenyl)sulfonyl)-1H-imidazol-5-yl)methanol

HRID 27613

Reaktionsgleichung

Reaktionsgleichung von HRID 27613
C(=O)(O)[O-].[Na+].Cl.[NH:7]1[C:11]([CH2:12][OH:13])=[CH:10][N:9]=[CH:8]1.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>O.C(OCC)(=O)C>[S:14]([N:7]1[C:11]([CH2:12][OH:13])=[CH:10][N:9]=[CH:8]1)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 122926Imidazol-4-ylmethanol hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 382151(1-((4-Methylphenyl)sulfonyl)-1H-imidazol-5-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To an ice cold solution of 0.08 mole of sodium bicarbonate in 40 ml of water is added 0.02 mole of imidazol-5-ylmethanol hydrochloride followed by a solution of 0.025 mole of tosylchloride in 30 ml of ethyl acetate. The reaction mixture is stirred at room temperature for 5 hours. The organic phase is separated, washed with sodium bicarbonate, and dried over magnesium sulfate and concentrated under reduced pressure. The residue is crystallized from ethyl acetate to afford 1-tosylimidazol-5-ylmethanol.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0234d9088d344fc98eb9e0fe5af5aad6
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221914

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