5-(Isocyanatomethyl)-1,2,3-trimethoxybenzene → 4-Oxo-3-(3,4,5-trimethoxybenzyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098287
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[CH2:6][N:7]=[C:8]=[O:9].[N+:17](=[C:19]1[N:23]=[CH:22][N:21]=[C:20]1[C:24]([NH2:26])=[O:25])=[N-:18]>CS(C)=O>[O:9]=[C:8]1[N:7]([CH2:6][C:5]2[CH:10]=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:18]=[N:17][C:19]2=[C:20]([C:24]([NH2:26])=[O:25])[N:21]=[CH:22][N:23]12

Komponenten

4

Edukt 2

HCID 51886915-(Isocyanatomethyl)-1,2,3-trimethoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Produkt 1

HCID 441283774-Oxo-3-(3,4,5-trimethoxybenzyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

3,4,5-Trimethoxybenzyl isocyanate (Sigma Aldrich) (0.536 g, 2.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product removed by filtration, washed with water and ethyl acetate, and then recrystallised from chloroform/hexane to give an off-white powder. Yield: 0.323 g, 45%. IR vmax/cm−1 1740, 1690, 1589. 1H NMR δH (DMSO-d6) 3.64 (3H, s, 4-OMe), 3.76 (6H, s, 3,5-OMe), 5.42 (2H, s, CH2Ar), 6.75 (2H, s, ArH), 7.68 (1H, br s, NH), 7.81 (1H, br s, NH), 8.84 (1H, s, 6-H). δC (DMSO-d6) 52.5, 56.4, 60.4, 105.9, 129.4, 131.3, 131.7, 134.9, 137.6, 139.7, 153.4, 162.0. MS Found 361.1300. Calc for (M+H): 361.1260. Found C, 49.5; H, 4.4; N, 23.2. Calc. for C15H16N6O5C, 50.0; H, 4.5; N, 23.3%.

Aufarbeitung

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product removed by filtration
  3. washwashed with water and ethyl acetate
  4. customrecrystallised from chloroform/hexane
  5. customto give an off-white powder

Quellen und Nachweise

ORD-Eintrag
ord-bf4469c4dffc43ff9189729f3a14c4a7
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450479B2

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