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

HRID 74154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74154
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 675026181-Phenyl-2-(phenylmethoxy)methylbenzimidazole-5-carboxylic acidAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a39ca48b12de47aa86d451dd84848e49
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

Notizen zur Reaktion

Wird geladen…