Water → HCID 68814476, compound

HRID 1436616Notes

Reaction equation

HRID 1436616 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-e25118b290b54978bd3c9afec1222817
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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