Pyridine → 3-[[5-Chloro-2-[[(chloromethyl)carbonyl]oxy]phenyl]methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one

HRID 1585477Notes

Reaction equation

HRID 1585477 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([OH:30])=[C:11]([CH2:13][N:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[O:16][C:15]2=[O:29])[CH:12]=1.N1C=CC=CC=1>ClCCl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:30][C:3]([CH2:2][Cl:1])=[O:4])=[C:11]([CH2:13][N:14]2[N:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:23][CH:24]=3)[O:16][C:15]2=[O:29])[CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 10474339Bms-191011

Product 1

HCID 212185933-[[5-Chloro-2-[[(chloromethyl)carbonyl]oxy]phenyl]methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-oneYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat chloroacetyl chloride (0.45 g, 5.6 mmol) was added dropwise to a stirred cold (0° C.) solution of 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one (1.8 g, 4.9 mmol) and anhydrous pyridine (0.45 g, 5.5 mmol) in anhydrous dichloromethane (30 mL). The resulting mixture was allowed to warm to room temperature and stirred for 4 hr. The dichloromethane was rotary evaporated and the residue was partitioned between diethylether-ethyl acetate and dilute HCl. The organic layer was washed with saturated sodium bicarbonate, water and brine and then dried (MgSO4). Evaporation of the solvents followed by recrystallization of the residue from acetone/hexanes afforded the title compound as off-white crystals (2.2 g, 98%). MS m/e 447 (MH+).

Workup

  1. customThe dichloromethane was rotary evaporated
  2. customthe residue was partitioned between diethylether-ethyl acetate and dilute HCl
  3. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvents
  6. customfollowed by recrystallization of the residue from acetone/hexanes

Sources & evidence

ORD record
ord-50058ab9d9434fdc92cf78e33d817393
Source dataset
uspto-grants-1999_08
Patent number
US05939405

Reaction notes

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