N-bromobutanimide → HCID 22285592, compound

HRID 1062459Notes

Reaction equation

HRID 1062459 reaction equation
[CH:1]1([CH2:4][C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH:4]([CH:1]1[CH2:3][CH2:2]1)[C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22285629Ethyl 3-cyclopropyl-2-oxopropanoate

Product 1

HCID 22285592HCID 22285592, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of ethyl 3-cyclopropyl-2-oxopropanoate (4.75 g, 30.44 mmol) in CCl4 (60 mL) at rt was added NBS (5.96 g 33.49 mmol). The resulting mixture was heated at reflux overnight, then cooled, filtered, and evaporated to provide ethyl 3-bromo-3-cyclopropyl-2-oxopropanoate; 1H NMR (CDCl3): δ 4.46-4.32 (3H, m), 1.41 (3H, t, J=8 Hz), 0.96-0.86 (1H, m), 0.55-0.50 (2H, m), 0.07-0.03 (2H, m). This compound was used without purification for the preparation of compounds of the invention such as 1-(4-chlorophenyl)-2-(2-chlorophenyl)-N-(1-piperidinyl)-5-cyclopropyl-1H-imidazole-4-carboxamide hydrochloride (Table entry 22). In a similar manner, ethyl 3-bromo-3-cyclobutyl-2-oxopropanoate and ethyl 3-bromo-3-isobutyl-2-oxopropanoate were prepared.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-803476ccc1fe450cbd4d67ae4b348dea
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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