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

HRID 2098286Notes

Reaction equation

HRID 2098286 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]=[C:7]=[O:8].[N+:13](=[C:15]1[N:19]=[CH:18][N:17]=[C:16]1[C:20]([NH2:22])=[O:21])=[N-:14]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]1[C:7](=[O:8])[N:19]2[CH:18]=[N:17][C:16]([C:20]([NH2:22])=[O:21])=[C:15]2[N:13]=[N:14]1

Participants

4

Reactant 2

HCID 45643971-(Isocyanatomethyl)-2-methoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 441283013-(2-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ortho-methoxybenzyl isocyanate (Sigma Aldrich) (0.390 g, 2.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry DMSO (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 (off-white) removed by filtration, washed with water and ethyl acetate then recrystallised from chloroform/hexane. Yield: 0.343 g, 57%. IR vmax/cm−1 3460, 3094, 1728, 1683, 1589, 1454. 1H NMR δH (DMSO-d6) 5.45 (2H, s, CH2Ar), 6.91 (1H, td, J 7.5, 0.8, ArH), 7.06 (1H, d, J 7.8, ArH), 7.27 (1H, d, J 7.5, 1.4, ArH), 7.30-7.33 (1H, m, ArH), 7.69 (1H, br s, NH), 7.81 (1H, br s, NH), 8.84 (1H, s, 6-H). δC 47.9, 56.0, 111.3, 120.7, 123.7, 129.1, 129.4, 129.7, 131.4, 134.9, 139.6, 157.1, 162.0. MS Found 301.1100. Calc for (M+H): 301.1049. Found C, 51.6; H, 3.9; N, 28.0. Calc. for C13H12N6O3C, 52.0; H, 4.0; N, 28.0%.

Workup

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

Sources & evidence

ORD record
ord-6a78ebedba1040db824c0c094917d5d7
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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