3-Bromoaniline → 1-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester

HRID 1661199Notes

Reaction equation

HRID 1661199 reaction equation
[CH2:1]([O:3][C:4](=[O:12])/[C:5](/[N+:10]#[C-:11])=[CH:6]/[N:7]([CH3:9])C)[CH3:2].[Br:13][C:14]1[CH:15]=C([CH:18]=[CH:19][CH:20]=1)N>C(O)CCC>[CH2:1]([O:3][C:4]([C:5]1[N:10]=[CH:11][N:7]([C:9]2[CH:18]=[CH:19][CH:20]=[C:14]([Br:13])[CH:15]=2)[CH:6]=1)=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 10975874HCID 10975874, compound

Product 1

HCID 161287541-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid ethyl esterYield 13%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of compound (Z)-3-dimethylamino-2-isocyano-acrylic acid ethyl ester (11.8 g, 79 mmol) and 3-bromo aniline (11.3 g, 65 mmol) in n-butanol (90 mL) was heated to reflux for 72 h [reaction was monitored by TLC]. Reaction mixture was concentrated under reduced pressure to remove n-butanol and the residue was passed through silica gel column, eluated with a mixture of ethyl acetate and hexane to give a mixture of ethyl and n-butyl ester compounds which was then separated by flash column chromatography over silica gel using 3:7 mixture ethyl acetate and hexane as eluant. Finally the ethyl ester was further purified by crystallization to furnish 3 (2.5 g, 13%) as a brown solid. HRMS (ESI+): m/z=295.1349 [M+H]

Workup

  1. temperatureto reflux for 72 h
  2. custom[reaction was monitored by TLC]
  3. customReaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customto remove n-butanol
  6. additioneluated with a mixture of ethyl acetate and hexane
  7. customto give
  8. customwas then separated by flash column chromatography over silica gel using 3:7 mixture ethyl acetate and hexane as eluant
  9. customFinally the ethyl ester was further purified by crystallization

Sources & evidence

ORD record
ord-55a28e001a51486698d0e8875ad2a7b8
Source dataset
uspto-grants-2011_10
Patent number
US08030339B2

Reaction notes

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