Ethanol → HCID 15457086, compound

HRID 992889Notes

Reaction equation

HRID 992889 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([Cl:13])=[CH:11][C:10]([F:14])=[C:9]([C:15]3[C:16](=[O:26])[N:17]([CH3:25])[C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)[C:7]=2[CH:8]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:32](O)[CH3:33]>>[Cl:13][C:12]1[C:6]2[O:5][C:4]([C:1]([O:3][CH2:32][CH3:33])=[O:2])=[CH:8][C:7]=2[C:9]([C:15]2[C:16](=[O:26])[N:17]([CH3:25])[C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)=[C:10]([F:14])[CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 15457194HCID 15457194, compound

Product 1

HCID 15457086HCID 15457086, compoundYield 99%

Procedure

0.08 g (0.21 mmol) of 3-(2-carboxy-7-chloro-5-fluorobenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 10 ml of ethanol, and 4.0 mg (0.04 mmol) of sulfuric acid was added thereto, followed by refluxing for 2 hours. Ethanol was distilled off under reduced pressure. Then, the obtained residue was poured into water and extracted with diethyl ether. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Diethyl ether was distilled off under reduced pressure. Then, the obtained crude crystals were washed with n-hexane to obtain 0.09 g (yield: 99%) of the desired product. Melting point: 118-120° C.

Workup

  1. temperatureby refluxing for 2 hours
  2. distillationEthanol was distilled off under reduced pressure
  3. additionThen, the obtained residue was poured into water
  4. extractionextracted with diethyl ether
  5. washAfter washing with water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. distillationDiethyl ether was distilled off under reduced pressure
  8. customThen, the obtained crude crystals
  9. washwere washed with n-hexane

Sources & evidence

ORD record
ord-aee1e53528a3435fbc02d13ebecbe448
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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