Sulfuric Acid → HCID 178459009, compound

HRID 508584Notes

Reaction equation

HRID 508584 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([CH:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[OH:10])=[N:8][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH:31](O)([CH3:33])[CH3:32]>>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([CH:9]([O:10][CH:31]([CH3:33])[CH3:32])[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:20])([F:19])[F:21])=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 178519719HCID 178519719, compound

Product 1

HCID 178459009HCID 178459009, compound

Conditions

Temperature
160 °C

Procedure

The compound of Example 1 (123 mg) was dissolved in isopropanol (2 mL), and concentrated sulfuric acid (41 mg) was added thereto. The mixture was heated at 140° C. for one hour and at 160° C. for 2 hours by means of a microwave reaction apparatus. The reaction mixture was basified with a 10% aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (10% to 100% ethyl acetate/hexane), and thus the title compound (66 mg) was obtained as a colorless solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (10% to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a52144bef1214fe598cc947fbd660e88
Source dataset
uspto-grants-2015_08
Patent number
US09096531B2

Reaction notes

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