Sodium Nitrite → HCID 178467500, compound

HRID 541362Notes

Reaction equation

HRID 541362 reaction equation
[CH:1]1([C:5]2[C:13]([C:14]3[NH:18][C:17]([O:19][CH2:20][CH3:21])=[N:16][N:15]=3)=[CH:12][C:8]([C:9](N)=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.N([O-])=[O:24].[Na+]>C(O)(C(F)(F)F)=O>[CH:1]1([C:5]2[C:13]([C:14]3[NH:18][C:17]([O:19][CH2:20][CH3:21])=[N:16][N:15]=3)=[CH:12][C:8]([C:9]([OH:24])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 178467490HCID 178467490, compound

Product 1

HCID 178467500HCID 178467500, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-cyclobutyl-5-(5-ethoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzamide (219.8, 0.1 g, 0.33 mmol) in TFA (5 ml) was added NaNO2 (0.046 g, 0.66 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour then at room temperature for 2 hours. The mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to give a clear oil. Yield: 0.1 g, 100%. m/z (ES−) 300 (M−H)−.

Workup

  1. waitat room temperature for 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between EtOAc and brine
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a clear oil

Sources & evidence

ORD record
ord-6b172f2c2c694d15b176d4bfd8310c24
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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