Реакция #161336

Уравнение реакции

3-amino-4-phenylaminobenzoic acid

benzyloxyacetyl chloride

→

title compound

Выход 86.8%

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

Выход 86.8%

Растворители

toluene

toluene

Условия реакции

Обработка

1. 1
   ДругоеA 4-neck flask equipped with a reflux condenser
2. 2
   Температураthis was refluxed
3. 3
   Экстракцияwas extracted with dilute aqueous sodium hydroxide solution (10%, 100 mL)
4. 4
   ПромывкаThis was washed with toluene
5. 5
   Другоеafter separating the dark orange aqueous layer
6. 6
   Температураthis was cooled (5 to 10° C.), and concentrated hydrochloric acid (12 M)
7. 7
   workup.ADDITIONwas added to the liquid
8. 8
   Другоеto give pH 4
9. 9
   ФильтрацияThe precipitated crystals were filtered off
10. 10
    Промывкаwashed with distilled water
11. 11
    Другоеdried under reduced pressure
12. 12
    Температураwith heating

Методика

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.

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