Sodium Nitrite → HCID 178494309, compound

HRID 1487982Notes

Reaction equation

HRID 1487982 reaction equation
[CH:1]1([C:5]2[C:13]([C:14]3[NH:18][C:17]([O:19][CH3:20])=[N:16][N:15]=3)=[CH:12][C:8]([C:9](N)=[O:10])=[C:7]([CH3:21])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.N([O-])=[O:23].[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][CH3:20])=[N:16][N:15]=3)=[CH:12][C:8]([C:9]([OH:23])=[O:10])=[C:7]([CH3:21])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 178494303HCID 178494303, compound2×

Product 1

HCID 178494309HCID 178494309, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-cyclobutyl-5-(5-methoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzamide (compound 89.8, 0.1 g, 0.33 mmol) in TFA (5 mL) at 0° C., was added NaNO2 (46 mg, 0.66 mmol). The mixture was stirred at 0° C. for 1 hour, then at room temperature for 2 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to yield 0.1 g (theoretical) of the title compound as a clear oil. m/z (ES+) 288 (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. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d43a31c1171d4774a6f376d63411d822
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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