4-Aminobenzoic Acid → 4-(1H-1,3-benzodiazol-2-yl)aniline

HRID 1781641

Reaktionsgleichung

Reaktionsgleichung von HRID 1781641
[2H][C:2]1[C:7]([2H])=[C:6]([NH2:9])[C:5]([NH2:10])=[C:4]([2H])[C:3]=1[2H].[NH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=O)=[CH:16][CH:15]=1>O.C(=O)([O-])[O-].[K+].[K+]>[NH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]2[NH:9][C:6]3[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=3[N:10]=2)=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 9784-Aminobenzoic AcidHCID 107729501,2-Diaminobenzene (D4, 98%)

Produkt 1

HCID 3456774-(1H-1,3-benzodiazol-2-yl)anilineAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

This intermediate was prepared according to the procedure given in E. Acalade et al., J. Org. Chem. 52:5009-15 (1987). A mixture of 3.21 g (0.0247 moles) of O-phenylenediamine, 3.93 g (0.0287 moles) of 4-aminobenzoic acid and 42 g of polyphosphoric acid was heated to 195° C. for 5 hours. After cooling to room temperature, the reaction mixture was diluted with 180 mL of water and basified to pH 8 with solid potassium carbonate. The resulting precipitate was collected, washed with water and dried to give 4.56 g of product.

Aufarbeitung

  1. customThis intermediate was prepared
  2. temperatureAfter cooling to room temperature
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-746b64fc659346af9a237e1ab8e9af1a
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05633388

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