Dimethyl Sulfoxide → 4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-YL]benzaldehyde

HRID 1268921Notes

Reaction equation

HRID 1268921 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][CH:12]([CH3:33])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=3)[N:21]=2)=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:11][CH:12]([CH3:33])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27][CH:26]=3)[N:21]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 11645224[4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol

Product 1

HCID 184469664-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-YL]benzaldehydeYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9.8 mL (112.4 mmol) of oxalyl chloride in 300 mL of dichloromethane was treated with 12 mL (168.6 mmol) of DMSO at −78° C. To the reaction mixture, 16.5 g of 4-(5-(4-(2-methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)phenylmethanol (from Step B) was added followed by 78 mL (450 mmol) of N,N-diisopropylethylamine at −78° C. The reaction mixture was allowed to warm to rt over 1 h. Dichloromethane was removed under reduced pressure and the residue was partitioned between ethyl acetate and 0.5 N KHSO4 solution. The organic layer was washed with 1 N HCl solution, saturated NaHCO3 and water and then was concentrated to dryness. The crude product was recrystallized from hexanes to afford 11.9 g of the title compound: 1H NMR (400 Mhz) δ 0.97 (d, J=6.7, 6H), 1.97 (m, 1H), 2.61 (d, J=7.0, 2H), 7.37 (d, J=8.0, 2H), 8.06 (d, J=8.2, 2H), 8.16 (d, J=8.2, 2H), 8.39 (d, J=8.0, 2H), 10.14 (s, 1H); ESI-MS 307 (M+1H); LC-1: 4.5 min.

Workup

  1. customDichloromethane was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 0.5 N KHSO4 solution
  3. washThe organic layer was washed with 1 N HCl solution, saturated NaHCO3 and water
  4. concentrationwas concentrated to dryness
  5. customThe crude product was recrystallized from hexanes

Sources & evidence

ORD record
ord-a9c960136467490d8b7be5b3cd52a802
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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