Hydrochloric Acid → 2-[(2,5-Dichloropyrimidin-4-yl)amino]benzamide

HRID 2091928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091928
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.Cl>CC(O)C>[Cl:11][C:12]1[N:17]=[C:16]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[C:15]([Cl:19])=[CH:14][N:13]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6942AnthranilamideHCID 2372592,4,5-Trichloropyrimidine

Produkt 1

HCID 579741762-[(2,5-Dichloropyrimidin-4-yl)amino]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-aminobenzamide (681 mg, 5.0 mmol), 2,4,5-trichloropyrimidine (2.75 g, 15 mmol, 3 equiv.) and concentrated HCl (aq) (1.72 mL, 20 mmol, 4 equiv.) in 2-propanol (100 mL) is heated at 60° C. for 12 h. The 2-propanol solvent is removed in vacuo. The resulting residue is neutralized to approximately pH=7 by adding 1 N NaOH (aq) followed by partition between EtOAc and water. Upon partition between EtOAc and water, a significant amount of precipitate is produced. This precipitate is collected by vacuum filtration and washed with small amounts of EtOAc and water, providing the product 2-(2,5-dichloropyrimidin-4-ylamino)benzamide; ESMS m/z 283.0 (M+H+).

Aufarbeitung

  1. customThe 2-propanol solvent is removed in vacuo
  2. additionby adding 1 N NaOH (aq)
  3. customby partition between EtOAc and water
  4. customUpon partition between EtOAc and water
  5. customa significant amount of precipitate is produced
  6. filtrationThis precipitate is collected by vacuum filtration
  7. washwashed with small amounts of EtOAc and water

Quellen und Nachweise

ORD-Eintrag
ord-487c29f2b1664b09bdc4c549ddda7e0d
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440681B2

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