Ethanol → Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

HRID 30621Notes

Reaction equation

HRID 30621 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]([O:11][CH2:12][CH3:13])=[O:10].C1(C)C(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=CC=1.[CH2:27](O)C>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:27]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:23][N:24]=[CH:25]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8025Ethyl formateHCID 97314-FluoroanilineHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 55563221Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylateYield 85%

Conditions

Temperature
65 °C

Procedure

A mixture of 4-fluoroaniline (11.1 g), ethyl formate (25.0 g) and ethanol (150 ml) was stirred at 65° C. for 2 hrs. Toluenesulfonylmethyl isocyanide (23.4 g) was added to the reaction mixture and the mixture was stirred for 2 hrs. with heating under reflux. The reaction mixture was concentrated and poured into water. The precipitated solids were collected by filtration, washed with water and dried to give ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (19.8 g, 85%). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 114-115° C.

Workup

  1. stirringthe mixture was stirred for 2 hrs
  2. temperaturewith heating
  3. temperatureunder reflux
  4. concentrationThe reaction mixture was concentrated
  5. additionpoured into water
  6. filtrationThe precipitated solids were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-4f17b4527f094b85a3aa5846bd4aaa2a
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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