4-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid → 2'-Methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-4-carbonyl chloride

HRID 131664

Reaction equation

HRID 131664 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([CH3:19])=[N:17][N:18]=2)=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([Cl:28])=[O:27])=[CH:22][CH:21]=1.CC1C=CC(C2OC(C)=NN=2)=CC=1C1C=CC(C(O)=O)=CC=1>CN(C=O)C.C(Cl)Cl>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([CH3:19])=[N:17][N:18]=2)=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([Cl:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic AcidHCID 865976482'-Methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-4-carbonyl chloride Oxalyl chloride

Product 1

HCID 210788012'-Methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1'-biphenyl-4-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carbonyl chloride Oxalyl chloride (0.073 ml, 0.82 mmol) was added to a suspension of 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (200 mg, 0.68 mmol), and DMF (2 drops) in DCM (10 ml) at 0° C. The reaction was stirred at room temperature for 1.5 h and the solvents evaporated under vacuum to give 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carbonyl chloride as a white solid (0.212 g, 100%). NMR; δH [2H6]—DMSO 8.03,(2H, d), 7.90,(1H, dd), 7.76,(1H, d), 7.56-7.53,(3H, m), 2.56,(3H, s), 2.30,(3H, s).

Workup

  1. customthe solvents evaporated under vacuum

Sources & evidence

ORD record
ord-f33f4b1536534a2da71d49b19363aef9
Source dataset
uspto-grants-2008_06
Patent number
US07384963B2

Linked notes

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