Phenethyl isocyanate → 4-Oxo-3-phenethyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098289Notes

Reaction equation

HRID 2098289 reaction equation
[CH2:1]([N:9]=[C:10]=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:12](=[C:14]1[N:18]=[CH:17][N:16]=[C:15]1[C:19]([NH2:21])=[O:20])=[N-:13]>CS(C)=O>[O:11]=[C:10]1[N:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:13]=[N:12][C:14]2=[C:15]([C:19]([NH2:21])=[O:20])[N:16]=[CH:17][N:18]12

Participants

4

Reactant 2

HCID 160602Phenethyl isocyanateHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 441285544-Oxo-3-phenethyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Phenethyl isocyanate (0.441 g, 3 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 (pale pink) was removed by filtration, washed with water and ethyl acetate, and recrystallised from chloroform to give the title compound. Yield: 0.259 g, 46%. IR vmax/cm−1 3132, 1743, 1668. 1H NMR δH (DMSO-d6) 3.14 (2H, t, J 7.4, CH2), 4.53 (2H, t, J 7.4, CH2), 7.21-7.33 (5H, m, ArH), 7.68 (1H, br s, NH), 7.81 (1H, br s, NH), 8.83 (1H, s, 6-H). δC 31.1, 34.6, 50.4, 127.1, 129.0, 129.2, 129.3, 131.2, 134.7, 138.2, 139.4, 162.0. MS Found 285.1161. Calc for (M+H): 285.1100. Found C, 55.0; H, 4.3; N, 29.4. Calc. for C13H12N6O3C 54.9; H 4.3; N, 29.6%.

Workup

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

Sources & evidence

ORD record
ord-260f8e5869e8456b98c9201fdb96c57a
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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