1,1-Dimethoxyethyl(dimethyl)amine → 3-(2-Bromo-4-chloro-6-fluorophenyl)-5-methyl-1,2,4-oxadiazole

HRID 1404556Notes

Reaction equation

HRID 1404556 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([F:13])[C:3]=1[C:4]([NH:6][OH:7])=[NH:5].CO[C:16](OC)(N(C)C)[CH3:17]>CC(O)C>[Br:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([F:13])[C:3]=1[C:4]1[N:5]=[C:16]([CH3:17])[O:7][N:6]=1

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 178513381HCID 178513381, compound

Product 1

HCID 684506413-(2-Bromo-4-chloro-6-fluorophenyl)-5-methyl-1,2,4-oxadiazoleYield 95.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-bromo-4-chloro-6-fluoro-N-hydroxy-benzamidine (26.5 g, 99.25 mmol) in 2-propanol (200 ml) was added N,N-dimethylacetamide dimethyl acetal (35.2 ml, 238.20 mmol) slowly at 25° C. and the reaction mixture was stirred for 30 minutes. After completion of the reaction all volatiles were evaporated and the resulting crude product was purified by chromatography (silica gel; hexane/EtOAc 97:3) to obtain the title compound as white solid (27.5 g, 58%). MS: m/z=290 [M]+.

Workup

  1. customAfter completion of the reaction all volatiles
  2. customwere evaporated
  3. customthe resulting crude product was purified by chromatography (silica gel; hexane/EtOAc 97:3)

Sources & evidence

ORD record
ord-86fcf8362b6147c5a7a3f9f7e48e21ac
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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