Trimethylamine → [[4-[[4-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenoxy]carbonyl]phenyl]-methyl] trimethylammonium chloride

HRID 617204Notes

Reaction equation

HRID 617204 reaction equation
[Cl:1][CH2:2][C:3]1[CH:35]=[CH:34][C:6]([C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[CH2:17][N:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[O:20][C:19]2=[O:33])=[O:8])=[CH:5][CH:4]=1.[CH3:36][N:37]([CH3:39])[CH3:38]>C(#N)C.C(OCC)(=O)C>[Cl-:1].[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:7]([C:6]2[CH:34]=[CH:35][C:3]([CH2:2][N+:37]([CH3:39])([CH3:38])[CH3:36])=[CH:4][CH:5]=2)=[O:8])=[C:11]([CH2:17][N:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=3)[O:20][C:19]2=[O:33])[CH:12]=1

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 218521004-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl 4-(chloromethyl)benzoate

Product 1

HCID 9808417[[4-[[4-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenoxy]carbonyl]phenyl]-methyl] trimethylammonium chlorideYield 72%

Reagents, catalysts & solvents 1

HCID 21930812Acetonitrile ethyl acetateSolvent

Procedure

A solution of 4-chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl 4-(chloromethyl)benzoate (0.3 g, 0.573 mmol) in acetonitrile/ethyl acetate (20 mL) was saturated with anhydrous trimethylamine. The reaction mixture was stirred at room temperature for two days. The precipitate was collected and purified by recrystallization from acetonitrile-ether to afford the title compound as a white solid (0.24 g, 72%):

Workup

  1. customThe precipitate was collected
  2. custompurified by recrystallization from acetonitrile-ether

Sources & evidence

ORD record
ord-64dfe40c41c147cd8fefffcf9919c0a9
Source dataset
uspto-grants-1999_09
Patent number
US05948802

Reaction notes

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