Isobutyryl chloride → HCID 69561203, compound

HRID 2121625Notes

Reaction equation

HRID 2121625 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][NH2:20])=[N:17][CH:18]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>ClCCl.CN(C=O)C.C(N(CC)C(C)C)(C)C>[CH3:1][C:2]1[O:3][C:4]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][NH:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])=[N:17][CH:18]=2)=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1

Participants

6

Reactant 2

HCID 62325Isobutyryl chloride2×HCID 23433766HCID 23433766, compound

Product 1

HCID 69561203HCID 69561203, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a stirred, cold (0° C.) solution of 5-(2-Methyl-4-phenyl-oxazol-5-yl)-pyridin-2-yl-hydrazine in 0.5 mL of dichloromethane and 0.3 mL of DMF and 0.325 mL of N,N-diisopropylethylamine was added 0.02 mL of isobutyryl chloride. After 5 minutes an additional 0.005 mL of isobutyryl chloride was added and the reaction was quenched a minute later with water. The mixture was extracted with dichloromethane (3×), washed with water (2×), brine (1×), dried (sodium sulfate), filtered, and the filtrate was concentrated to a dark orange oil. This oil was purified by flash chromatography (eluting with 5:1 ethyl acetate/hexanes) to give 23 mg of isobutyric acid N′-[5-(2-methyl-4-phenyl-oxazol-5-yl)-pyridin-2-yl]-hydrazide as an orange solid.

Workup

  1. customthe reaction was quenched a minute later with water
  2. extractionThe mixture was extracted with dichloromethane (3×)
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to a dark orange oil
  7. customThis oil was purified by flash chromatography (eluting with 5:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-03b4b94eb1c044b38b49b59985dd5b7e
Source dataset
uspto-grants-2004_02
Patent number
US06696464B2

Reaction notes

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