Pyridine → 4-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl 4-(chloromethyl)benzoate

HRID 617203Notes

Reaction equation

HRID 617203 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([OH:36])=[C:17]([CH2:19][N:20]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[O:22][C:21]2=[O:35])[CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:36][C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][C:17]=2[CH2:19][N:20]2[N:24]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)[O:22][C:21]2=[O:35])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 10474339Bms-191011

Product 1

HCID 218521004-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl 4-(chloromethyl)benzoateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(chloromethyl)benzoyl chloride (2.24 g, 11.9 mmol) in methylene chloride (25 mL) was added to a cold (0° C.) stirred suspension of 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one (4.0 g, 10.8 mmol) and pyridine (0.96 mL, 11.9 mmol) in methylene chloride (25 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with 1 N HCl and extracted with ethyl acetate (100 mL). The organic layer was separated and washed with sat'd NaHCO3, water, brine and then dried (MgSO4). Evaporation of the solvent gave the crude product which was recrystallized from methylene chloride/hexanes to afford the title compound as white crystals (4.8 g, 85%): mp 142-144° C.; MS m/e: 523 (MH+).

Workup

  1. stirringstirred overnight
  2. customThe reaction was quenched with 1 N HCl
  3. extractionextracted with ethyl acetate (100 mL)
  4. customThe organic layer was separated
  5. washwashed with sat'd NaHCO3, water, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customgave the crude product which
  9. customwas recrystallized from methylene chloride/hexanes

Sources & evidence

ORD record
ord-1db4b5b9f4ad479ea2a6466acdb0fdd2
Source dataset
uspto-grants-1999_09
Patent number
US05948802

Reaction notes

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