Dimethylformamide → HCID 22729294, compound

HRID 460585Notes

Reaction equation

HRID 460585 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-4e79c1e082cf4b74aca96e21da50aaa3
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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