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Triethylamine → 2-Chloro-5-[5-(4-isobutylphenyl)-1,3,4-oxadiazol-2-yl]pyridine

HRID 2242213
Notes
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Reaction equation

HRID 2242213 reaction equation
[Cl-].C[N+](C)=CS(Cl)(=O)=O.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][N:12]=1.[CH2:20]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([NH:30][NH2:31])=O)=[CH:26][CH:25]=1)[CH:21]([CH3:23])[CH3:22].C(N(CC)CC)C>ClCCl>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]2[O:17][C:28]([C:27]3[CH:32]=[CH:33][C:24]([CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=3)=[N:30][N:31]=2)=[CH:13][N:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 15710081(Chlorosulfonyl)-N,N-dimethylmethaniminium chlorideHCID 207719354-Isobutylbenzohydrazide

Product 1

HCID 592042812-Chloro-5-[5-(4-isobutylphenyl)-1,3,4-oxadiazol-2-yl]pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

N,N-Dimethyl(chlorosulphonyl)methaniminium chloride (1.57 g, 0.01 mol) was added to a solution of 6-chloronicotinic acid (1.58 g, 0.01 mol) and dichloromethane (20 mL) at 0° C. and stirred for 10 minutes. 4-isobutylbenzohydrazide (5.29 g, 0.03 mol) was added to the reaction mixture, followed by the dropwise addition of a solution of triethylamine (12.3 mL, 0.09 mol) in dichloromethane (30 mL). The resulting mixture was stirred at room temperature for 12 hours, quenched with water (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4) and concentrated in vacuo. The resulting residue was recrystallized from methanol:acetone (10:1) to give the title compound (2.57 g, 82% yield) as a white solid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 12 hours
  2. customquenched with water (50 mL)
  3. extractionextracted with dichloromethane (2×50 mL)
  4. washThe combined organic extracts were washed with water (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was recrystallized from methanol:acetone (10:1)

Sources & evidence

ORD record
ord-6544087cdd5f47cd84d2b9f6f58dca19
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07671043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes