Hydrochloric Acid → HCID 21105753, compound

HRID 1354458Notes

Reaction equation

HRID 1354458 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)=[N:12][N:11]=1)([O-:3])=[O:2].P([O-])(O)(O)=[O:24].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O.O1CCCC1.C(O)(C)(C)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:24])=[O:20])=[CH:21][CH:22]=2)=[N:12][N:11]=1)([O-:3])=[O:2]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 24437Sodium SulfiteHCID 21105752HCID 21105752, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 21105753HCID 21105753, compoundYield 102%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzaldehyde (0.930 g), sodium dihydrogen phosphate (0.490 g), 2-methyl-2-butene (1.95 ml), t-butanol (20 ml), tetrahydrofuran (20 ml) and water (20 ml) was added sodium chlorite (0.570 g) at 0° C., and the mixture was stirred for 3 hrs. To the mixture was added an aqueous sodium sulfite solution, and the mixture was stirred at room temperature for 15 min., and acidified by adding 1 M hydrochloric acid. The crystals were collected by filtration to give 4-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (1.00 g, yield 78%). Recrystallization from hexane-tetrahydrofuran gave pale-yellow prism crystals. melting point: 239–240° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min.
  2. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-299e15ec5268454681dc0a1f960efb6f
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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