1-Methyl-4-nitro-1H-imidazole-2-carbonyl chloride → HCID 19108632, Verbindung

HRID 327425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327425
[CH3:1][N:2]([NH:4][C:5]([C:7]1[N:8]([CH3:13])[CH:9]=[C:10]([NH2:12])[N:11]=1)=[O:6])[CH3:3].[CH3:14][N:15]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[C:16]1[C:23](Cl)=[O:24]>C1COCC1.C(Cl)Cl>[CH3:3][N:2]([NH:4][C:5]([C:7]1[N:8]([CH3:13])[CH:9]=[C:10]([NH:12][C:23]([C:16]2[N:15]([CH3:14])[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=2)=[O:24])[N:11]=1)=[O:6])[CH3:1]

Komponenten

5

Edukt 2

HCID 191086291-Methyl-4-nitro-1H-imidazole-2-carbonyl chlorideHCID 19108657HCID 19108657, Verbindung

Produkt 1

HCID 19108632HCID 19108632, VerbindungAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

The amine from above was dissolved in dry THF (20 mL) and cooled to -20° C. The stirring reaction mixture was placed under argon and a solution of 1-methyl-4-nitroimidazole-2-carbonyl chloride (2.18 g, 11.5 mmol) in dry CH2Cl2 (10 mL) was added dropwise. The reaction was allowed to warm to room temperature and stirred overnight then concentrated to dryness and water was added. The suspension was filtered and the solid was washed with carbon tetrachloride and water, then dried in-vacuo (80° C.) to provide N-(N',N'-dimethylamino)-1-methyl-4-[1-methyl-4-nitroimidazole-2-carboxamido]imidazole-2-carboxamide as a pale yellow crystalline solid, 2.18 g (68.8% yield). A sample for analysis was obtained by recrystallization from water: mp 239° C. (dec.). TLC (5% MeOH/CHCl3) Rf 0.66. 1H--NMR (CDCl3); δ2.69 (s, 6H, N(CH3)2), 4.07 (s, 3H, N--CH3), 4.21 (s, 3H, N--CH3), 7.43 (s, 1H, NH). IR (nujol: υ3397 and 1678 cm-1. MS(El) m/z (rel. intensity) 336 (M+, 100), 293 (M+1-N(CH3)2, 85).

Aufarbeitung

  1. customThe stirring reaction mixture
  2. temperatureto warm to room temperature
  3. concentrationthen concentrated to dryness and water
  4. additionwas added
  5. filtrationThe suspension was filtered
  6. washthe solid was washed with carbon tetrachloride and water
  7. customdried in-vacuo (80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-144a0aa00bbe4581a4783800f13bf03a
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273991

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