Acetic Acid → HCID 9808135, compound

HRID 381266Notes

Reaction equation

HRID 381266 reaction equation
[N:1]1([C:6]2[CH:19]=[CH:18][C:9]([C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[C:27][CH2:28][O:29][C:30](=[O:35])/[CH:31]=[C:32](\[NH2:34])/[CH3:33])[CH:21]=1.[CH:36](=O)[CH:37]=[CH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O)(=O)C>CO>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[C:27][CH2:28][O:29][C:30]([C:31]2[CH:36](/[CH:37]=[CH:38]/[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([C:9]3[CH:18]=[CH:19][C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[CH:7][CH:8]=3)[NH:34][C:32]=2[CH3:33])=[O:35])[CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3073-Phenylprop-2-EnalHCID 22142503HCID 22142503, compoundHCID 70211242HCID 70211242, compound

Product 1

HCID 9808135HCID 9808135, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

520 mg of ethyl 4-(1-imidazolyl)benzoylacetate, 420 mg of 3-aminocrotonate 3-(3-pyridyl)-2-propynylester, and 300 mg of cinnamaldehyde were allowed to stand in 20 ml methanol solution containing 1 ml of acetic acid at room temperature for 1 week. The reaction solution was extracted with ethyl acetate and then the solvent was concentrated to dryness. The oily substance was purified by silica gel column chromatography to obtain the target compound in an amount of 520 mg (48.2%).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. concentrationthe solvent was concentrated to dryness
  3. customThe oily substance was purified by silica gel column chromatography
  4. customto obtain the target compound in an amount of 520 mg (48.2%)

Sources & evidence

ORD record
ord-d985c4d5bddc4a07863d043a8ebdb94f
Source dataset
uspto-grants-2001_10
Patent number
US06306853B1

Reaction notes

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