Acetic Acid → HCID 18616879, Verbindung

HRID 1263538

Reaktionsgleichung

Reaktionsgleichung von HRID 1263538
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH3:12][C:13]1[C:14]([NH2:20])=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1.[ClH:21].Cl.[C:23](=N)(OCC)[CH2:24][C:25](=N)OCC.C(O)(=O)C>Cl>[ClH:21].[ClH:21].[CH3:12][C:13]1[C:14]2[N:20]=[C:23]([CH2:24][C:25]3[NH:1][C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=4[N:11]=3)[NH:19][C:15]=2[CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 175932,3-DiaminotolueneHCID 73106Diethyl malonimidateHCID 43595253-Nitro-1,2-phenylenediamine

Produkt 1

HCID 18616879HCID 18616879, VerbindungAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

The following components were reacted according to General Procedure 1, above: 3-nitro-1,2-phenylenediamine (0.5 g; 3.26 mmoles), 3-methyl-1,2-phenylenediamine (0.4 g; 3.26 mmoles), diethyl malonimidate dihydrochloride (1.1 eq.; 0.83 g; 3.60 mmoles) and acetic acid (25 mL). The crude mixture of three compounds was then reduced according to General Procedure 2, above. The crude solid product was taken up in 10 mL of dilute HCl, purified by preparative HPLC (15 to 75% acetonitrile (with 0.1% TFA) over 60 minutes) and converted to the HCl salt by three freeze drying cycles with dilute HCl. This procedure gave 0.42 g of pure 2-[(4-methyl-1H-benzimidazol-2-yl)methyl]-1H-benzimidazol-4-ylamine dihydrochloride in 37% yield. It had MS: m/z=278.2 [N+1] amu and gave one peak on HPLC at both 210 and 280 nm (12.01 minutes using the JWTFACN gradient).

Aufarbeitung

  1. customThe following components were reacted
  2. additionThe crude mixture of three compounds
  3. custompurified by preparative HPLC (15 to 75% acetonitrile (with 0.1% TFA) over 60 minutes)
  4. dry with materialdrying cycles with dilute HCl

Quellen und Nachweise

ORD-Eintrag
ord-3409410321724b4ba1a2df2c75a03243
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541486B1

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