Acetic Anhydride → (1-((4-Methylphenyl)sulfonyl)-1H-imidazol-5-yl)methyl acetate

HRID 27614

Reaction equation

HRID 27614 reaction equation
[S:1]([N:11]1[C:15]([CH2:16][OH:17])=[CH:14][N:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)(Cl)Cl>[C:25]([O:17][CH2:16][C:15]1[N:11]([S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:12]=[N:13][CH:14]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 382151(1-((4-Methylphenyl)sulfonyl)-1H-imidazol-5-yl)methanol

Product 1

HCID 382152(1-((4-Methylphenyl)sulfonyl)-1H-imidazol-5-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 10 mmole of 1-tosylimidazol-5-ylmethanol in 10 ml of chloroform is added dropwise 20 mmole of triethylamine followed by the addition of 13 mmole of acetic anhydride over a period of 2 hours. Stirring is continued for 5 hours at 25° C. after which the solvent is removed under reduced pressure. The residue is partitioned between ethyl acetate and water. The organic phase is washed with sodium bicarbonate, dried over magnesium sulfate and evaporated under vacuo. Recrystallization of the residue from ethyl acetate yields 5-acetoxymethyl-1-tosylimidazole.

Workup

  1. customafter which the solvent is removed under reduced pressure
  2. customThe residue is partitioned between ethyl acetate and water
  3. washThe organic phase is washed with sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuo
  6. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-a3aec77526df4621ac4e8bf28147b8e9
Source dataset
uspto-grants-1980_09
Patent number
US04221914

Linked notes

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