Diphenyl Ether → HCID 178469883, compound

HRID 624637Notes

Reaction equation

HRID 624637 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6](=[NH:16])[NH:7]OC=CC(OCC)=O)=[C:4]([F:19])[CH:3]=1.CC([O:24]C)(C)C.[C:26]1([O:32][C:33]2[CH:38]=CC=CC=2)C=CC=[CH:28][CH:27]=1>>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[NH:7][CH:28]=[C:27]([C:26]([O:32][CH2:33][CH3:38])=[O:24])[N:16]=2)=[C:4]([F:19])[CH:3]=1

Participants

4

Reactant 3

HCID 7583Diphenyl EtherHCID 15413tert-Butyl methyl etherHCID 178472242HCID 178472242, compound2×

Product 1

HCID 178469883HCID 178469883, compound

Procedure

A solution of ethyl 3-(4-bromo-2-fluorobenzimidamidooxy)acrylate 25 (300 g, 0.91 mol, 1 eq) in diphenyl oxide (900 mL, 3 vol) was stirred at 190° C. under N2 for 1 h and checked by LC-MS (no 25 remaining) Cooled the mixture to rt and TBME (600 mL, 2 vol of 25) was added, and then PE (1.8 L, 6 vol of 25) was dropwise added to separate out solids. The mixture was stirred at rt for 20 min, and filtered to give 160 g wet cake. The wet cake was washed with PE (1 L) and dried to afford 120 g ethyl 2-(4-bromo-2-fluorophenyl)-1H-imidazole-4-carboxylate 26 with 92% LC purity as brown solids.

Workup

  1. customto separate out solids
  2. filtrationfiltered
  3. customto give 160 g wet cake
  4. washThe wet cake was washed with PE (1 L)
  5. customdried

Sources & evidence

ORD record
ord-54fa55ef9ee24905b9bc435c9571093e
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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