Hydrochloric Acid → 2-Amino-3-nitro-6-(2,2,2-trifluoro-ethoxy)-benzoic acid ethyl ester

HRID 18615

Reaktionsgleichung

Reaktionsgleichung von HRID 18615
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[CH2:9]([O:11][C:12](=[O:24])[C:13]1[C:18](F)=[CH:17][CH:16]=[C:15]([N+:20]([O-:22])=[O:21])[C:14]=1[NH2:23])[CH3:10].Cl>C1COCC1>[CH2:9]([O:11][C:12](=[O:24])[C:13]1[C:18]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])=[CH:17][CH:16]=[C:15]([N+:20]([O-:22])=[O:21])[C:14]=1[NH2:23])[CH3:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 2756434Benzoic acid, 2-amino-6-fluoro-3-nitro-, ethyl ester

Produkt 1

HCID 686161072-Amino-3-nitro-6-(2,2,2-trifluoro-ethoxy)-benzoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

420 mg NaH (60% suspension in oil) were added to a solution of 2.16 mL (29.8 mmol) 2,2,2-trifluoro-ethanol in 5 mL THF. When the gas evolution ceased, 1.0 g (4.38 mmol) 2-Amino-6-fluoro-3-nitro-benzoic acid ethyl ester was added. The resulting mixture was stirred at 0° C. for 30 minutes and at room temperature for further 30 minutes. To this mixture were added 2 mL of a 6 M aqueous HCl-solution, and most of the solvent was removed under reduced pressure. The residue was mixed with 20 mL water and the resulting solid was collected and washed with water and then hexane. The obtained yellow crystalline material was dried under reduced pressure at 35° C. Yield: 1.22 g.

Aufarbeitung

  1. custommost of the solvent was removed under reduced pressure
  2. additionThe residue was mixed with 20 mL water
  3. customthe resulting solid was collected
  4. washwashed with water
  5. customThe obtained yellow crystalline material was dried under reduced pressure at 35° C

Quellen und Nachweise

ORD-Eintrag
ord-72e6377cac6543abae76d361f020c377
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741341B2

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