Chloroform → HCID 67050219, compound

HRID 2103844Notes

Reaction equation

HRID 2103844 reaction equation
[CH3:1][NH:2][N:3]=[CH:4][C:5](=[O:7])[CH3:6].[Br:8][C:9]1[CH:10]=[C:11]([C:16](=O)[CH:17]=[O:18])[CH:12]=[CH:13][C:14]=1[F:15].C(Cl)(Cl)Cl.CCCCCC.C(OCC)(=O)C>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([C:16]2[N:2]([CH3:1])[N:3]=[C:4]([C:5](=[O:7])[CH3:6])[C:17]=2[OH:18])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 21226206Ethyl acetate hexaneHCID 22273591HCID 22273591, compoundHCID 727702682-Oxopropanal methylhydrazone

Product 1

HCID 67050219HCID 67050219, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Oxopropanal methylhydrazone (10.56 mmol, 1.06 g) and (3-bromo-4-fluorophenyl)(oxo)acetaldehyde (10.56 mmol, 2.44 g) synthesized in Reference Synthetic Example 9 were dissolved in acetic acid (37 mL) and stirred at 100° C. for 4.5 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=3/1) to give the desired product as a brown solid (160 mg, yield 5%).

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-2b58f808e7304226b159a20fc9841aeb
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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