Isobutyryl chloride → HCID 69561320, compound

HRID 2121622Notes

Reaction equation

HRID 2121622 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([NH:18][NH2:19])=[N:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>ClCCl>[C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([NH:18][NH:19][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])=[N:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 23433719HCID 23433719, compound

Product 1

HCID 69561320HCID 69561320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(4-Phenyl-oxazol-5-yl)-pyridin-2-yl-hydrazine (2.5 g, 9.9 mmol), and N,N-diisopropylethylamine (8.6 mL, 50 mmol) in dichloromethane (8 mL) at 0° C. was added dropwise isobutyryl chloride (1.04 mL, 9.9 mmol); the mixture was stirred at 0° C. for 2 hours. The reaction was quenched with water and extracted with dichloromethane (3×). The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered, and the filtrate was concentrated in vacuo to a dark sticky solid. The residue was purified by flash chromatography (eluting with ethyl acetate/hexanes 3:1) to give the title compound as a yellow solid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo to a dark sticky solid
  7. customThe residue was purified by flash chromatography (eluting with ethyl acetate/hexanes 3:1)

Sources & evidence

ORD record
ord-5d6b0a8e723047bba29e9f1584e5556c
Source dataset
uspto-grants-2004_02
Patent number
US06696464B2

Reaction notes

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