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Hydrochloric Acid → 4-amino-N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]benzamide;dihydrochloride

HRID 547556
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 547556
[ClH:1].Cl.[NH2:3][C:4](=[N:6]/[N:7]=[C:8](/[C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH:13]=[CH:14][CH:15]=1)\[CH3:9])[NH2:5].CCO.Cl>[Fe].O>[ClH:1].[ClH:1].[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10](/[C:8](=[N:7]/[N:6]=[C:4]([NH2:5])[NH2:3])/[CH3:9])[CH:11]=2)=[O:27])=[CH:23][CH:22]=1
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Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 87307446N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]-4-nitrobenzamide;dihydrochloride

Produkt 1

HCID 873068154-amino-N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]benzamide;dihydrochlorideAusbeute 212,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925
Iron
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a refluxing suspension of amide F4 (2.02 g, 5.36 mmol) in 2:1 EtOH:H2O (100 mL) were sequentially added Fe dust (1.20 g, 21.44 mmol) and c.HCl (2 mL), and the resulting suspension was refluxed for 14 h. After this time, the hot reaction mixture was filtered through a pad of Celite, and the solvent was removed under reduced pressure. The residue was re-dissolved in hot H2O, and the resulting suspension filtered through a pad of Celite. Solvent was removed under reduced pressure, and the residue dried via three MeOH-azeotrope cycles. The resulting residue was reprecipitated from acidified MeOH to afford triamine F5 (2.18 g, quantitative) as an amorphous cream solid; 1H NMR (400 MHz, DMSO): δ 11.30 (s, 1H, hydrazonyl-N+—H), 10.05 (s, 1H, ArC(O)NHAr), 8.21 (s, 1H, ArH), 8.20-7.55 (m, 8H, ArH & ═C(NH2)2), 7.36 (t, J=7.90 Hz, 1H, ArH), 6.91 (d, J=7.96 Hz, 1H, ArH), 5.30 (v br s, 3H, ArNH3+), 2.35 (s, 3H, Ar(CH3)═N—); LCMS (APCI+): 311 (100%).

Aufarbeitung

  1. filtrationAfter this time, the hot reaction mixture was filtered through a pad of Celite
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was re-dissolved in hot H2O
  4. filtrationthe resulting suspension filtered through a pad of Celite
  5. customSolvent was removed under reduced pressure
  6. dry with materialthe residue dried via three MeOH-azeotrope cycles
  7. customThe resulting residue was reprecipitated

Quellen und Nachweise

ORD-Eintrag
ord-b3bba3f84c3b48399cef1fffec8f06b8
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07939546B2

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