Triethylamine → HCID 59532610, compound

HRID 1924426Notes

Reaction equation

HRID 1924426 reaction equation
C(N(CC)CC)C.[CH2:8]([S:10][C:11]1[CH:33]=[CH:32][CH:31]=[CH:30][C:12]=1[C:13]([NH:15][NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=1)=O)[CH3:9].[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl>[CH2:8]([S:10][C:11]1[CH:33]=[CH:32][CH:31]=[CH:30][C:12]=1[C:13]1[O:29][C:17]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=2)=[N:16][N:15]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 595326112-(ethylthio)-N'-(4-pentylbenzoyl)benzohydrazide

Product 1

HCID 59532610HCID 59532610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (735 μL, 5.28 mmol) was added to a stirring solution of 2-(ethylthio)-N′-(4-pentylbenzoyl)benzohydrazide (1-D) (326 mg, 0.88 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (448 mg, 2.64 mmol) in methylene chloride (10 mL). After stirring at room temperature for 18 h, the mixture was diluted with methylene chloride and washed with water, 1N HCl, 10% NaHCO3, brine, dried (MgSO4) and evaporated in vacuo. The oily residue was purified by preparative TLC (silica gel, hexane:ethyl acetate, 4:1) to provide 2-[2-(ethylthio)phenyl]-5-(4-pentylphenyl)-1,3,4-oxadiazole (1-E).

Workup

  1. washwashed with water, 1N HCl, 10% NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe oily residue was purified by preparative TLC (silica gel, hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-5c8ae20e8519461a9c9b9b4060c25d2a
Source dataset
uspto-grants-2012_05
Patent number
US08178546B2

Reaction notes

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