Hydrochloric Acid → 2-(2,2,2-Trifluoro-1-hydroxy-ethyl)-6-trifluoromethyl-1H-benzimidazole-5-carbonitrile

HRID 230455

Reaktionsgleichung

Reaktionsgleichung von HRID 230455
[NH2:1][C:2]1[C:9]([NH2:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[F:15][C:16]([F:23])([F:22])[CH:17]([OH:21])[C:18](O)=O.Cl.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[F:15][C:16]([F:23])([F:22])[CH:17]([C:18]1[NH:1][C:2]2[CH:3]=[C:4]([C:11]([F:12])([F:13])[F:14])[C:5]([C:6]#[N:7])=[CH:8][C:9]=2[N:10]=1)[OH:21]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acidHCID 516892Sodium BicarbonateHCID 529919264,5-Diamino-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 866350472-(2,2,2-Trifluoro-1-hydroxy-ethyl)-6-trifluoromethyl-1H-benzimidazole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
108 °C

Versuchsvorschrift

4,5-Diamino-2-trifluoromethyl-benzonitrile (4.14 g; 20.6 mmoles) and 3,3,3-trifluoro-2-hydroxy-propionic acid (4.50 g; 31.2 mmoles) were suspended in 6N HCl (7 mL; 42 mmoles) under a nitrogen atmosphere. The reaction was stirred vigorously and heated to 108° C. for 18 hrs, then cooled to room temperature. The reaction was diluted with water (100 mL) and with ethyl acetate (100 mL), then sodium bicarbonate (5.19 g; 62.0 mmoles) was added slowly and in portions to quench the reaction. The aqueous layer was separated and extracted with ethyl acetate (3×40 mL). The extracts were combined, washed with water (30 mL) and brine (30 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo to yield a crude dark solid which was then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as a dark brown solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customto quench
  3. customthe reaction
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate (3×40 mL)
  6. washwashed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto yield a crude dark solid which
  10. customwas then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-c18a7d1784284cc087d5396fc1692a5b
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566733B2

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