631912-32-8 → HCID 44128894, compound

HRID 2098306Notes

Reaction equation

HRID 2098306 reaction equation
[N+:1](=[C:3]1[N:7]=[CH:6][N:5]=[C:4]1[C:8]([NH2:10])=[O:9])=[N-:2].[N:11]([CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]=[O:13]>CS(C)=O>[CH3:19][S:16]([CH2:15][CH2:14][N:11]1[C:12](=[O:13])[N:7]2[CH:6]=[N:5][C:4]([C:8]([NH2:10])=[O:9])=[C:3]2[N:1]=[N:2]1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 21886681631912-32-8HCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128894HCID 44128894, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-diazoimidazole-4-carboxamide (0.5 g, 12.0 mmol) in dry DMSO (5 mL) was added 1-Isocyanato-2-methanesulfonyl-ethane (1.04 g, 3.65 mmol). The mixture was stirred at room temperature for 16 hours, whereupon it was poured onto crushed ice and the resultant precipitate collected by filtration. The filter cake was washed with Et2O (3×1 reaction volume) and dried to give the title compound as an off white solid (990 mg, 95%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.89 (1H, s), 7.84 (1H, s), 7.71 (1H, s), 4.73 (2H, t, J=6.8 Hz), 3.70 (2H, t, j=6.8 Hz), 2.44 (3H, s).

Workup

  1. additionwas poured
  2. customonto crushed ice
  3. filtrationthe resultant precipitate collected by filtration
  4. washThe filter cake was washed with Et2O (3×1 reaction volume)
  5. customdried

Sources & evidence

ORD record
ord-a771a0df68c54393924c065b943950f2
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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