Chloroacetic Acid → 2-(chloromethyl)-5,6-difluoro-1H-1,3-benzodiazole

HRID 1788288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788288
[F:1][C:2]1[C:3](N)=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[F:8].[Cl:11][CH2:12][C:13](O)=O.[NH4+:16].[OH-]>Cl>[Cl:11][CH2:12][C:13]1[NH:9][C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[CH:6][C:5]=2[N:16]=1

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 14923Ammonium HydroxideHCID 27367533,4-Difluorobenzene-1,2-diamine

Produkt 1

HCID 180713122-(chloromethyl)-5,6-difluoro-1H-1,3-benzodiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1 g of 3,4-difluoro-1,2-phenylenediamine (6.94 mmol) and 0.983 g of chloro-acetic acid (10.41 mmol, 1.5 eq) in 13 mL of 4N aqueous HCl was heated to 100° C. for 3 h. The mixture was poured onto ice (10 g), neutralized by the addition of NH4OH and extracted with three 30 mL portions of ethyl acetate. The organic extracts were combined and dried over Na2SO4, filtered and concentrated by rotary evaporation to give 1.28 g of 2-chloromethyl-5,6-difluoro-1H-benzoimidazole as a brown solid. 1H NMR (300 MHz, CDCl3/CD3OD): δ 7.30-7.25 (m, 2H), 4.68 (s, 2H); MS (ESI): Calcd m/z for C8H5ClF2N2.H+=203.1. Found m/z=203.2/205.2 [(M+1)+/(M+3)+].

Aufarbeitung

  1. additionThe mixture was poured onto ice (10 g)
  2. extractionextracted with three 30 mL portions of ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-aa810b331fbb4e18a986c0027bc5c8c1
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511146B2

Notizen zur Reaktion

Wird geladen…