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

HRID 27613

Reaction equation

HRID 27613 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0234d9088d344fc98eb9e0fe5af5aad6
Source dataset
uspto-grants-1980_09
Patent number
US04221914

Linked notes

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