Dimethylformamide → HCID 68861944, compound

HRID 2109406Notes

Reaction equation

HRID 2109406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[CH:11][O:10][C:9]=2[C:20]([NH:22][NH2:23])=[O:21])=[CH:4][CH:3]=1.CN([CH:27]=[O:28])C>C(OCC)(=O)C>[C:20]([C:9]1[CH:8]=[C:12]([CH:13]=[CH:14][C:27]=1[OH:28])[C:11]([NH:23][NH:22][C:20]([C:9]1[O:10][CH:11]=[C:12]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:21])=[O:10])#[N:22]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 68863693HCID 68863693, compound

Product 1

HCID 68861944HCID 68861944, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,4-bis(4-chlorophenyl)-2-furancarboxylic acid hydrazide (compound of Reference Example 36, 0.092 g) and the compound of Reference Example 63 (0.11 g) in DMF (5 ml) was stirred overnight at 70° C. The reaction solution was diluted with ethyl acetate, washed with water, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: 1:20 methanol/chloroform), and recrystallized from ethyl acetate/hexane, thereby giving 0.054 g of the desired compound. Melting point: 190-191° C. (Recrystallized from ethyl acetate)

Workup

  1. customwas stirred overnight at 70° C
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: 1:20 methanol/chloroform)
  6. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7a26ac7a1fa04f1a960279181d9aa6a0
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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