Imidazole → (S)-Imidazol-1-YL-(tetrahydrofuran-2-YL)-methanone

HRID 1517646Notes

Reaction equation

HRID 1517646 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[O:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11](Cl)=[O:12]>C(Cl)(Cl)Cl>[N:1]1([C:11]([C@@H:7]2[CH2:8][CH2:9][CH2:10][O:6]2)=[O:12])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 42131216(S)-tetrahydrofuran-2-carbonyl chloride

Product 1

HCID 57741232(S)-Imidazol-1-YL-(tetrahydrofuran-2-YL)-methanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

21.8 g (32.0 mmol) imidazole are placed in 400 ml chloroform and cooled to 0° C. 21.5 g (15.0 mmol) (S)-tetrahydrofuran-2-carbonyl chloride are added dropwise, then stirred for 1.5 hours at ambient temperature. After cooling again to 0° C. the reaction mixture is extracted with semisaturated sodium chloride solution. The organic phase is dried and evaporated to dryness. Yield: 23.5 g

Workup

  1. temperatureAfter cooling again to 0° C. the reaction mixture
  2. extractionis extracted with semisaturated sodium chloride solution
  3. customThe organic phase is dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-85cc9b530a604b86a74f8f2a157213c9
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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