Acetoxyacetyl chloride → 2-Acetoxymethyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid

HRID 74163

Reaction equation

HRID 74163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:5]([OH:7])=[O:6].[C:18]([O:21][CH2:22][C:23](Cl)=O)(=[O:20])[CH3:19]>O1CCOCC1>[C:18]([O:21][CH2:22][C:23]1[N:11]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 548880483-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acid

Product 1

HCID 674979142-Acetoxymethyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4-neck flask (1 L) equipped with a reflux condenser was charged with 3-amino-4-((tetrahydropyran-4-yl)amino)benzoic acid (14.53 g, 45.65 mmol) and anhydrous 1,4-dioxane (226 mL) and this was refluxed. Acetoxyacetyl chloride (12.57 g, 92.07 mmol) in 1,4-dioxane solution (100 mL) was added dropwise to this over approx. 15 minutes. This was stirred under these conditions for 13 hours. This was allowed to cool to room temperature, and after the precipitated crystals were filtered off, they were washed with distilled water, and dried under reduced pressure with heating to yield the title compound (13.46 g, 92.6% yield) as a white solid.

Workup

  1. customA 4-neck flask (1 L) equipped with a reflux condenser
  2. temperaturethis was refluxed
  3. filtrationafter the precipitated crystals were filtered off
  4. washthey were washed with distilled water
  5. customdried under reduced pressure
  6. temperaturewith heating

Sources & evidence

ORD record
ord-94f7055b52004583b0d1e4aaa332f9e0
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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