Sulfuric Acid → HCID 59730230, compound

HRID 925224Notes

Reaction equation

HRID 925224 reaction equation
N[C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[OH:19]S(O)(=O)=O.N([O-])=O.[Na+]>O>[F:13][C:12]([F:15])([F:14])[C:11]([N:8]1[CH2:9][CH2:10][C:4]2[CH:3]=[C:2]([OH:19])[CH:18]=[CH:17][C:5]=2[CH2:6][CH2:7]1)=[O:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 18943538HCID 18943538, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 59730230HCID 59730230, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

Into a 250 ml flask, the product of step (c) (2 g, 7.75 mmol) dissolved in water (8.5 ml) and concentrated H2SO4 (1.5 ml) was added. The stirred mixture was heated to 70° C., followed by the addition of a solution NaNO2 (615 mg, 8.91 mmol) in water (20 ml). The reaction mixture was stirred at 70° C. for 1 hour. The mixture was then allowed to cool to room temperature and diluted with water (50 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the sub-title compound as a brown solid (1.8 g) that was used without further purification. MS: ESI (positive): 260 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous mixture was extracted with EtOAc (3×)
  3. washThe combined EtOAc extracts were washed with brine
  4. dry with materialdried over Na2SO4, and solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9efc7799939a4bf59895cb943dcdfbbf
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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