Water → 2-(3,4-Diethoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazole

HRID 447894

Reaction equation

HRID 447894 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[N:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:15][NH2:16])=[O:14])=[CH:9][CH:8]=1.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[C:23](Cl)=O)[CH3:18].O>CN1C(=O)CCC1>[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([C:23]2[O:14][C:13]([C:10]3[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=3)=[N:15][N:16]=2)[CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 3767IsoniazidHCID 10340Sodium CarbonateHCID 27582343,4-Diethoxybenzoyl chloride

Product 1

HCID 8564702-(3,4-Diethoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a stirred suspension of Na2CO3 (1.42 mmol, 150.52 mg) and pyridine-4-carbohydrazide (0.71 mmol, 97 mg) in NMP (0.8 mL) was added a solution of 3,4-diethoxybenzoylchloride (prepare above) in NMP (0.8 mL). The reaction was stirred for 12 h at room temperature, poured to 20 mL of cold H2O and filtered. The precipitated intermediate was dried in vacuo. The solid was added to POCl3 (5 mL) and heated to 70-72° C. for 6 h. The solution was poured in an ice-water container and neutralized with a solution of NaOH (2M). The precipitated product was filtered and purified by C.C. using CH2Cl2:MeOH (9:1) to yield the product in 67% yield (150 mg).

Workup

  1. filtrationfiltered
  2. customThe precipitated intermediate was dried in vacuo
  3. additionThe solid was added to POCl3 (5 mL)
  4. temperatureheated to 70-72° C. for 6 h
  5. additionThe solution was poured in an ice-water container
  6. filtrationThe precipitated product was filtered
  7. custompurified by C.C
  8. customusing CH2Cl2:MeOH (9:1) to yield the product in 67% yield (150 mg)

Sources & evidence

ORD record
ord-0041ff7a4dfd4beba4b9fe8621d5d4a5
Source dataset
uspto-grants-2013_07
Patent number
US08481573B2

Linked notes

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