Acetic Acid → Methyl 2-bromo-5-(1-hydroxy-2-nitro-ethyl)-3-(3-methyl-2-buten-1-yl)-3H-imidazole-4-carboxylate

HRID 230107Notes

Reaction equation

HRID 230107 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:11][C:12]1[N:16]([CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:15]([C:22]([O:24][CH3:25])=[O:23])=[C:14]([CH:26]=[O:27])[N:13]=1.C(O)(=O)C>CO.C(Cl)Cl>[Br:11][C:12]1[N:16]([CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:15]([C:22]([O:24][CH3:25])=[O:23])=[C:14]([CH:26]([OH:27])[CH2:4][N+:1]([O-:3])=[O:2])[N:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 10796Cesium carbonateHCID 11580300methyl 2-bromo-3-(3-methyl-2-buten-1-yl)-5-formyl-3H-imidazole-4-carboxylate

Product 1

HCID 67435131Methyl 2-bromo-5-(1-hydroxy-2-nitro-ethyl)-3-(3-methyl-2-buten-1-yl)-3H-imidazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

35 ml nitromethane are added to 1.14 g caesium carbonate in 15 ml of methanol at ambient temperature. Then the mixture is combined with a solution of 3.50 g methyl 2-bromo-3-(3-methyl-2-buten-1-yl)-5-formyl-3H-imidazole-4-carboxylate in 20 ml of methanol and 5 ml methylene chloride and stirred for 15 minutes at ambient temperature. Then 0.5 ml acetic acid are added and the solution is evaporated down in vacuo. The flask residue is combined with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and evaporated down.

Workup

  1. customthe solution is evaporated down in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-b5dc9be678934c9a91f1e26dcc687f46
Source dataset
uspto-grants-2009_07
Patent number
US07566707B2

Reaction notes

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