Chloroform → HCID 67050300, compound

HRID 2103850Notes

Reaction equation

HRID 2103850 reaction equation
[CH3:1][NH:2][N:3]=[CH:4][C:5](=[O:7])[CH3:6].[CH2:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH:21]=[O:22])=[CH:16][CH:15]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(Cl)(Cl)Cl.CCCCCC.C(OCC)(=O)C>C(O)(=O)C>[CH2:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:2]([CH3:1])[N:3]=[C:4]([C:5](=[O:7])[CH3:6])[C:21]=2[OH:22])=[CH:16][CH:15]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 15323737HCID 15323737, compoundHCID 21226206Ethyl acetate hexaneHCID 727702682-Oxopropanal methylhydrazone

Product 1

HCID 67050300HCID 67050300, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Oxopropanal methylhydrazone (16.1 mmol, 1.62 g) and (4-n-hexylphenyl)(oxo)acetaldehyde (16 mmol, 4.57 g) synthesized in Reference Synthetic Example 14 were dissolved in acetic acid (35 mL) and stirred at 100° C. for 6 hours. Then, the solvent was evaporated, and the residue was dried by means of a vacuum pump and purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1), then by silica gel thin layer chromatography (chloroform) and by silica gel thin layer chromatography (n-hexane/ethyl acetate=7/2) to give the desired product as a brown solid (308 mg, yield 6%).

Workup

  1. customThen, the solvent was evaporated
  2. customthe residue was dried by means of a vacuum pump
  3. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-e7da87f3fb594cb0896f06803ebda1dc
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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