Hydrochloric Acid → HCID 21105735, compound

HRID 1354457Notes

Reaction equation

HRID 1354457 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:11][N:10]=2)=[CH:5][CH:4]=1.P([O-])(O)(O)=[O:25].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O.O1CCCC1.C(O)(C)(C)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[C:17]([OH:25])=[O:18])=[N:11][N:10]=2)=[CH:5][CH:4]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 24437Sodium SulfiteHCID 21105734HCID 21105734, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 21105735HCID 21105735, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzaldehyde (0.800 g), sodium dihydrogen phosphate (0.300 g), 2-methyl-2-butene (1.2 ml), t-butanol (10 ml), tetrahydrofuran (20 ml) and water (10 ml) was added sodium chlorite (0.570 g) at 0° C., and the mixture was stirred for 2 hrs. To the mixture was added aqueous sodium sulfite solution, and the mixture was stirred at room temperature for 30 min., acidified by adding 1 M hydrochloric acid, and extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 3-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.730 g, yield 87%). Recrystallization from hexane-tetrahydrofuran gave colorless prism crystals. melting point: 239–240° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min.
  2. extractionextracted with ethyl acetate-tetrahydrofuran
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf39dd326a16413ebfb8d78fa278bac7
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

Loading…