Acetic Acid → HCID 66643683, compound

HRID 1923560Notes

Reaction equation

HRID 1923560 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][CH:7]=1)=[O:5])[CH3:2].C(OC(=O)C)(=O)C.C(O)(=O)C.[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[CH:35]=O>O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](/[CH:11]=[CH:35]/[C:25]2[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:27][O:28][C:24]=2[CH3:23])=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 27761445-Methyl-3-phenylisoxazole-4-carboxaldehydeHCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 66643683HCID 66643683, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

2-Methyl-thiazole-5-carboxylic acid ethyl ester (547 mg, 2.92 mmol) was dissolved in acetic anhydride (0.15 mL, 15.5 mmol) and acetic acid (0.04 mL, 2.54 mmol) then 5-methyl-3-phenyl-4-isoxazolecarbaldehyde (500 mg, 2.92 mmol) was added and the reaction mixture warmed to 120° C. After 6 days, the reaction mixture was cooled to room temperature then diluted with water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 30% ethyl acetate in heptane) to give the title compound (191 mg, 19%) as an off-white solid after trituration with isopropylether. MS: m/e=341.3 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthen purified by chromatography (silica, 0 to 30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-44193f3d90e4415c8471e640b89b2615
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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