Sodium Nitrite → HCID 59094528, compound

HRID 1168293Notes

Reaction equation

HRID 1168293 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]2[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15](=S)[NH:16][N:17]=2)[O:4]1.N([O-])=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]2[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[N:16][N:17]=2)[O:4]1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 59094532HCID 59094532, compound

Product 1

HCID 59094528HCID 59094528, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-benzyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (Preparation 18) (2.2 g, 6.1 mmol) in acetic acid (30 ml) was treated portionwise with sodium nitrite (1.2 g, 18 mmol) over 30 minutes. After an additional 30 minutes, the solvent was removed by evaporation under reduced pressure and the residue was suspended in acetone (30 ml). The insoluble inorganic salts were removed by filtration and the filtrate was evaporated under reduced pressure. The residue was then dissolved in dichloromethane (30 ml), the mixture was filtered again and the filtrate was evaporated under reduced pressure to give the title compound (2.0 g).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customThe insoluble inorganic salts were removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was then dissolved in dichloromethane (30 ml)
  5. filtrationthe mixture was filtered again
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d84bc5c6bd0d4a9d84eed77f588c2745
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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