4-Diazo-4H-imidazole-5-carboxamide → HCID 44128467, compound

HRID 2098300Notes

Reaction equation

HRID 2098300 reaction equation
[N:1]([CH2:4][C:5]1[O:9][N:8]=[C:7]([CH3:10])[CH:6]=1)=[C:2]=[O:3].[N+:11](=[C:13]1[N:17]=[CH:16][N:15]=[C:14]1[C:18]([NH2:20])=[O:19])=[N-:12]>CS(C)=O>[CH3:10][C:7]1[CH:6]=[C:5]([CH2:4][N:1]2[C:2](=[O:3])[N:17]3[CH:16]=[N:15][C:14]([C:18]([NH2:20])=[O:19])=[C:13]3[N:11]=[N:12]2)[O:9][N:8]=1

Participants

4

Reactant 2

HCID 534265854-Diazo-4H-imidazole-5-carboxamideHCID 59567456134517-52-5

Product 1

HCID 44128467HCID 44128467, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

5-Isocyanatomethyl-3-methyl-isoxazole (735 mg, 5.32 mmol) was diluted in DMSO (1.5 mL) and added to a solution of 5-diazoimidazole-4-carboxamide (250 mg, 1.83 mmol) in 2 mL DMSO. The reaction mixture was stirred at room temperature for 16 hours before the addition of sufficient ice water to cause precipitation of the crude product which was collected by vacuum filtration and washed with Et2O (1 reaction volume title compound as a yellow solid (503 mg, 98% yield). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.86 (1H, s), 7.84 (1H, s), 7.71 (1H, s), 6.51 (1H, s), 5.64 (2H, s), 2.21 (3H, s).

Workup

  1. customprecipitation of the crude product which
  2. filtrationwas collected by vacuum filtration
  3. washwashed with Et2O (

Sources & evidence

ORD record
ord-eecc681afa584283b7643de9f0f82251
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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