1-(Isocyanatomethyl)-2,4-dimethoxybenzene → 3-(2,4-Dimethoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098291
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[CH2:5][N:6]=[C:7]=[O:8].[N+:15](=[C:17]1[N:21]=[CH:20][N:19]=[C:18]1[C:22]([NH2:24])=[O:23])=[N-:16]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[CH2:5][N:6]1[C:7](=[O:8])[N:21]2[CH:20]=[N:19][C:18]([C:22]([NH2:24])=[O:23])=[C:17]2[N:15]=[N:16]1

Komponenten

4

Edukt 2

HCID 112525271-(Isocyanatomethyl)-2,4-dimethoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Produkt 1

HCID 441283793-(2,4-Dimethoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

2,4-dimethoxybenzyl isocyanate (0.717 g, 4.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.548 g, 4 mmol) in dry dimethylsulfoxide (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 (purple) removed by filtration, washed with water and ethyl acetate and recrystallised from chloroform/hexane to give the title compound. Yield: 0.613 g, 46%. IR vmax/cm−1 3473, 3121, 1734, 1697, 1605, 1589. 1H NMR δH (DMSO-d6) 3.76 (3H, s, OMe), 3.80 (3H, s, OMe), 5.37 (2H, s, CH2Ar), 6.48 (1H, dd, J=8.4, 2.4, ArH), 6.60 (1H, d, J=2.4, ArH), 7.22 (1H, d, J=8.4, ArH), 7.68 (1H, br s, NH), 7.80 (1H, br s, NH), 8.81 (1H, s, 6-H). δC (DMSO-d6) 47.5, 55.8, 56.1, 98.9, 105.1, 115.9, 129.3, 130.7, 131.2, 134.8, 139.4, 158.5, 161.1, 162.0.

Aufarbeitung

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product (purple) removed by filtration
  3. washwashed with water and ethyl acetate
  4. customrecrystallised from chloroform/hexane

Quellen und Nachweise

ORD-Eintrag
ord-33fb9dfe688c41969a7a542961502fc1
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450479B2

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