3,5-Diaminobenzoic acid → HCID 20217438, Verbindung

HRID 235789

Reaktionsgleichung

Reaktionsgleichung von HRID 235789
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:12]([BH3-])#[N:13].[Na+]>CO>[NH2:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([NH:13][CH2:12][CH:2]2[CH2:3][CH2:4][CH2:8][CH2:9][CH2:10]2)[CH:10]=1)[C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 2

HCID 120623,5-Diaminobenzoic acidHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 20217438HCID 20217438, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

15.2 g. (0.1 mol) of 3,5-diaminobenzoic acid was placed in a 500 ml. round bottom flask to which 200 ml. of methanol was added. To the round bottom flask 11.22 g. (0.1 mol) of cyclohexane carboxyaldehyde was added. The solution was stirred for several minutes. While the solution stirred, 3.77 g. (0.06 mol) sodium cyanoborohydride was added slowly. After 5 hours the solution was filtered and then concentrated to dryness. The reaction mixture was dissolved in 200 ml. of 2M hydrochloric acid. The acid solution was extracted twice with 200 ml. ethyl acetate. The ethyl acetate solutions were combined and back washed with 200 ml. distilled water, and then dried over sodium sulfate. The solution was concentrated to dryness and 4.18 gm. of product was collected. The product was then purified by column chromatography using a solution of tetrahydrofuran/ethanol/water/ammonium hydroxide in the following ratio--10:3:1:0.04 as the eluent. Structural verification was obtained by carbon magnetic resonance, proton magnetic resonance and infra-red analysis.

Aufarbeitung

  1. stirringWhile the solution stirred
  2. filtrationAfter 5 hours the solution was filtered
  3. concentrationconcentrated to dryness
  4. dissolutionThe reaction mixture was dissolved in 200 ml
  5. extractionThe acid solution was extracted twice with 200 ml
  6. washback washed with 200 ml
  7. dry with materialdistilled water, and then dried over sodium sulfate
  8. concentrationThe solution was concentrated to dryness and 4.18 gm
  9. customof product was collected
  10. customThe product was then purified by column chromatography
  11. customStructural verification was obtained by carbon magnetic resonance, proton magnetic resonance and infra-red analysis

Quellen und Nachweise

ORD-Eintrag
ord-720368e702464072a5aecef68611657b
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642240

Verknüpfte Notizen

Wird geladen…