Sulfuric Acid → HCID 53986262, compound

HRID 2258625Notes

Reaction equation

HRID 2258625 reaction equation
[CH2:1]([NH:4][C:5]1[CH:11]=[C:10]([NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]([F:18])=[CH:8][C:6]=1[NH2:7])[CH:2]=[CH2:3].S(=O)(=O)(O)O.[N:24]([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([N:4]1[C:5]2[CH:11]=[C:10]([NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]([F:18])=[CH:8][C:6]=2[N:7]=[N:24]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 22921558HCID 22921558, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 53986262HCID 53986262, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A stirred solution of 3.5 grams (0.014 mole) of 2-(2-propen-1-ylamino)-4-ethoxycarbonylamino-5-fluoroaniline in 100 mL of aqueous 1% sulfuric acid was cooled to about -5° C., and a solution of 1.9 grams (0.028 mole) of sodium nitrite dissolved in a minimum of water was added dropwise, while the reaction mixture temperature was held at about 0°-10° C. Upon completion of the addition, the reaction mixture was stirred for one hour and then poured into water. The mixture was made basic to a pH of 8 with potassium carbonate. The mixture was then extracted thoroughly with ethyl acetate. The combined extracts were washed with an aqueous solution saturated with sodium chloride, and then dried with magnesium sulfate. The mixture was filtered, and the filtrate was subjected to column chromatography on silica gel. Elution was accomplished with 1:3 ethyl acetate in hexane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of 1-(2-propen-1-yl)-5-fluoro-6-ethoxycarbonylaminobenzotriazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added dropwise, while the reaction mixture temperature
  2. customwas held at about 0°-10° C
  3. additionUpon completion of the addition
  4. extractionThe mixture was then extracted thoroughly with ethyl acetate
  5. washThe combined extracts were washed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe mixture was filtered
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81938e26e6bf4275b4ada6a5cf30be60
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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