Sodium Hydroxide → HCID 772300, compound

HRID 919367Notes

Reaction equation

HRID 919367 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+].[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=O>CC1CCCO1.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:7]=[C:31]([C:27]3[O:26][CH:30]=[CH:29][CH:28]=3)[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 682422-Furancarbonyl chlorideHCID 2246504-chloro-N'-hydroxybenzenecarboximidamide

Product 1

HCID 772300HCID 772300, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 73012-MethyltetrahydrofuranSolvent

Procedure

The 4-chlorobenzamidoxime (1.24 g, 7.25 mmol) was dissolved in 2-methyltetrahydrofuran (10.0 mL) and water (1.0 mL). A 40% aqueous solution of benzyltrimethylammonium hydroxide (100 uL) and 50% aqueous solution of sodium hydroxide (736 mg, 9.20 mmol) were added. The mixture was stirred and a precipitate formed. Furoyl chloride (1.24 g, 7.25 mmol) was added dropwise and an exotherm was noted. The mixture was stirred at 70° C. for 1 hour and cooled to room temperature. The solution was poured into water (25 mL) and the 2-methyltetrahydrofuran removed at reduced pressure. The resulting solids were isolated by vacuum filtration. The 3-(4-chlorophenyl)-5-(2-furanyl)-1,2,4-oxadiazole (1.22 g, 4.94 mmol) was obtained as a white solid. (68% yield).

Workup

  1. customa precipitate formed
  2. stirringThe mixture was stirred at 70° C. for 1 hour
  3. customthe 2-methyltetrahydrofuran removed at reduced pressure
  4. customThe resulting solids were isolated by vacuum filtration

Sources & evidence

ORD record
ord-73453280f90a4772bf575750ab6912e9
Source dataset
uspto-grants-2016_03
Patent number
US09273037B2

Reaction notes

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