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

HRID 2098288Notes

Reaction equation

HRID 2098288 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]=[C:8]=[O:9].[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:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]1[C:8](=[O:9])[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 36446341-(Isocyanatomethyl)-3-methoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 441283783-(3-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Meta-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 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 (off-white) removed by filtration, washed with water and ethyl acetate, and recrystallised from chloroform. Yield: 0.335 g, 56%. IR vmax/cm−1 3092, 1730, 1678, 1601. 1H NMR δH (DMSO-d6) 3.76 (3H, s, Me), 5.49 (2H, s, CH2Ar), 6.89-6.92 (1H, m, ArH), 7.00-7.02 (1H, m, ArH), 7.28-7.32 (1H, s, ArH), 7.70 (1H, br s, NH), 7.82 (1H, br s, NH), 8.84 (1H, s, 6-H). δC (DMSO-d6) 52.2, 55.6, 113.7, 114.0, 120.4, 129.5, 130.1, 131.4, 134.9, 137.6, 139.7, 159.9, 162.0. Found 301.1091. Calc for (M+H): 301.1049. Found C, 51.3; H 3.9; N 27.8. 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. customrecrystallised from chloroform

Sources & evidence

ORD record
ord-cdd16747ee244d7eaed8ddc9b311da1c
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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