2-Bromopropane → Isopropyl 1-isopropyl-2-bromo-4-methyl-5-imidazolecarboxylate

HRID 986344Notes

Reaction equation

HRID 986344 reaction equation
[Br:1][C:2]1[NH:3][C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.N1(C2CCCCCCCCCC2)CCCCCC[CH2:18][CH2:17][CH2:16]N1.BrC(C)C>C1C=CC=CC=1>[CH:17]([N:3]1[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=[C:2]1[Br:1])([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 57346892DiazabicycloundecaneHCID 178432453HCID 178432453, compound

Product 1

HCID 13645929Isopropyl 1-isopropyl-2-bromo-4-methyl-5-imidazolecarboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2 g (8.1×10-3 moles) of isopropyl 2-bromo-4-methyl-5-imidazolecarboxylate in 20 ml of benzene was added 1.2 ml (8.2×10-3 moles) of diazabicycloundecane, followed by 1.0 g. (8.1×10-3 moles) of 2-bromopropane. The resulting mixture was heated to reflux overnight, cooled to room temperature and filtered. Concentration in vacuo gave a golden oil. This residue was purified by medium pressure liquid chromatography on silica gel to yield 1.6 g (70%) isopropyl 1-isopropyl-2-bromo-4-methyl-5-imidazolecarboxylate as a yellow oil, but only 466 milligrams (20%) of the desired product, isopropyl 2-bromo-3-isopropyl-4-methyl-5-imidazolecarboxylate (also a yellow oil), wherein S1 and S3 and R were all CH(CH3)2.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationConcentration in vacuo
  5. customgave a golden oil
  6. customThis residue was purified by medium pressure liquid chromatography on silica gel

Sources & evidence

ORD record
ord-0ece8a023fe3485493ae804340359378
Source dataset
uspto-grants-1987_12
Patent number
US04711962

Reaction notes

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