Water → HCID 68814476, compound

HRID 732473Notes

Reaction equation

HRID 732473 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[F:18])[C:6]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])=[O:7])#N.[OH2:19].S(=O)(=O)(O)[OH:21]>>[F:18][C:17]1[C:3]([C:1]([OH:21])=[O:19])=[CH:4][C:5]([C:6]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])=[O:7])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 68814479HCID 68814479, compound

Product 1

HCID 68814476HCID 68814476, compound

Conditions

Temperature
150 °C

Procedure

Dissolve 3-cyano-4-fluoro-N,N-dipropylbenzamide (0.52 g, 2.1 mmol) in a 3:1 solution of concentrated sulfuric acid:water (5 mL). Heat at 150° C. until no starting material remains. Cool to room temperature, pour into water and extract with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride solution, dry (magnesium sulfate) and concentrate to give the title compound that is used without further purification.

Workup

  1. temperatureCool to room temperature
  2. extractionextract with ethyl acetate
  3. washWash the organic layer with saturated aqueous sodium chloride solution
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-c9e009ed699f446fb83c4b168e2d1315
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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