Citric Acid → HCID 68108180, compound

HRID 385127Notes

Reaction equation

HRID 385127 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[C:21]=1[O:22][CH3:23])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[CH2:9]1)=[O:7])=[O:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:31].CC(=CC)C.Cl([O-])=O.[Na+]>CO>[O:18]=[S:10]1(=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]([C:6]([C:5]2[CH:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[C:21]([O:22][CH3:23])=[C:3]([CH:4]=2)[C:1]([OH:31])=[O:2])=[O:7])[CH2:9]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86668180HCID 86668180, compound

Product 1

HCID 68108180HCID 68108180, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-formyl-4-methoxy-5-trifluoromethylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (248 mg) was dissolved in methanol (2.5 mL) and an aqueous 10% citric acid solution (2.5 mL), and 2-methyl-2-butene (0.33 mL) and sodium chlorite (84 mg) were added to the solution, and then the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure and 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% sodium thiosulfate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (277 mg) as a pale yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and 1N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous 10% sodium thiosulfate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-85c9d0e3c38d4c3ca608bb51a9f9638f
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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