Benzyloxyacetyl chloride → 1-Phenyl-2-(phenylmethoxy)methylbenzimidazole-5-carboxylic acid

HRID 74154Notes

Reaction equation

HRID 74154 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[CH2:18]([O:25][CH2:26][C:27](Cl)=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:12]1([N:11]2[C:10]3[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=3[N:1]=[C:27]2[CH2:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 177085Benzyloxyacetyl chlorideHCID 7738213-Amino-4-phenylamino-benzoic acid

Product 1

HCID 675026181-Phenyl-2-(phenylmethoxy)methylbenzimidazole-5-carboxylic acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 4-neck flask equipped with a reflux condenser was charged with 3-amino-4-phenylaminobenzoic acid (see Synthesis Example 1-2) (3.09 g, 13.54 mmol) and anhydrous toluene (45 mL) and this was refluxed. To this was added dropwise benzyloxyacetyl chloride (5 g, 27.08 mmol) in toluene solution (approx. 3 mL) over approx. 10 minutes. This was stirred under these conditions for 15 hours. This was allowed to cool to room temperature, and was extracted with dilute aqueous sodium hydroxide solution (10%, 100 mL). This was washed with toluene, and after separating the dark orange aqueous layer, this was cooled (5 to 10° C.), and concentrated hydrochloric acid (12 M) was added to the liquid to give pH 4. The precipitated crystals were filtered off, washed with distilled water, and dried under reduced pressure with heating to yield the title compound (4.21 g, 86.8% yield) as a light purple powder.

Workup

  1. customA 4-neck flask equipped with a reflux condenser
  2. temperaturethis was refluxed
  3. extractionwas extracted with dilute aqueous sodium hydroxide solution (10%, 100 mL)
  4. washThis was washed with toluene
  5. customafter separating the dark orange aqueous layer
  6. temperaturethis was cooled (5 to 10° C.), and concentrated hydrochloric acid (12 M)
  7. additionwas added to the liquid
  8. customto give pH 4
  9. filtrationThe precipitated crystals were filtered off
  10. washwashed with distilled water
  11. customdried under reduced pressure
  12. temperaturewith heating

Sources & evidence

ORD record
ord-a39ca48b12de47aa86d451dd84848e49
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

Loading…