Sodium Hydroxide → HCID 867607, compound

HRID 919366Notes

Reaction equation

HRID 919366 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+].[S: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[S: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 789282-Thiophenecarbonyl chlorideHCID 2246504-chloro-N'-hydroxybenzenecarboximidamide

Product 1

HCID 867607HCID 867607, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The 4-chlorobenzamidoxime (1.00 g, 5.8 mmol) was dissolved in 2-methyltetrahydrofuran (10.0 mL) and water (1.0 mL). A 40% aqueous solution of benzyltrimethylammonium hydroxide (100 uL) was added and the solution heated to 50° C. A 50% aqueous solution of sodium hydroxide (720 mg, 9.00 mmol) and 2-thiophenecarbonyl chloride (939.0 mg, 6.4 mmol) were added dropwise simultaneously over 15 minutes. The temperature of the mixture warmed to 70° C. The mixture was cooled to room temperature and water (40 mL) added. Solids formed and the 2-methyltetrahydrofuran was removed at reduced pressure. The solids were isolated by vacuum filtration. The 3-(4-chlorophenyl)-5-(2-thienyl)-1,2,4-oxadiazole (1.32 g, 5.0 mmol) was obtained as a white solid. (86% yield).

Workup

  1. temperatureThe temperature of the mixture warmed to 70° C
  2. temperatureThe mixture was cooled to room temperature
  3. customSolids formed
  4. customthe 2-methyltetrahydrofuran was removed at reduced pressure
  5. customThe solids were isolated by vacuum filtration

Sources & evidence

ORD record
ord-066df9260d2b4e1882eaa9666ec9bc65
Source dataset
uspto-grants-2016_03
Patent number
US09273037B2

Reaction notes

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