Dimethylformamide → HCID 22729294, compound

HRID 2085157Notes

Reaction equation

HRID 2085157 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([C:12]([NH:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=O)=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.S(Cl)(Cl)=O.CN(C=O)C>ClCCCl>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([C:12]3[O:21][C:16]([C:17]([F:18])([F:19])[F:20])=[N:15][N:14]=3)=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22729221HCID 22729221, compound

Product 1

HCID 22729294HCID 22729294, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution (280 ml) of N′-(7-methoxybenzo(b)furan-2-ylcarbonyl)trifluoroacetohydrazide (14.6 g) in 1,2-dichloroethane were added thionyl chloride (4.2 ml) and DMF (0.1 ml) and the mixture was refluxed under heating for 4.5 hr. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform/ethyl acetate) to give the title compound (2.4 g) as pale-yellow crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4.5 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-e8093b2c098e4488bd5d1967eff2b1cb
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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