반응 #161336

반응 방정식

3-amino-4-phenylaminobenzoic acid

benzyloxyacetyl chloride

→

title compound

수율 86.8%

1-phenyl-2-(phenylmethoxy)methylbenzimidazole-5-carboxylic acid

수율 86.8%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타A 4-neck flask equipped with a reflux condenser
2. 2
   온도this was refluxed
3. 3
   추출was extracted with dilute aqueous sodium hydroxide solution (10%, 100 mL)
4. 4
   세척This was washed with toluene
5. 5
   기타after separating the dark orange aqueous layer
6. 6
   온도this was cooled (5 to 10° C.), and concentrated hydrochloric acid (12 M)
7. 7
   workup.ADDITIONwas added to the liquid
8. 8
   기타to give pH 4
9. 9
   여과The precipitated crystals were filtered off
10. 10
    세척washed with distilled water
11. 11
    기타dried under reduced pressure
12. 12
    온도with heating

실험 절차

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.

출처