HCID 22728911, compound → HCID 22728937, compound

HRID 2085153Notes

Reaction equation

HRID 2085153 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:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([C:12]3[O:23][C:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[N:15][N:14]=3)=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 22728911HCID 22728911, compound

Product 1

HCID 22728937HCID 22728937, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

N′-(7-Methoxybenzo(b)furan-2-ylcarbonyl)benzohydrazide (5.0 g) was dissolved in thionyl chloride (20 ml) and the mixture was stirred with heating at 80° C. for 1 hr. Thionyl chloride was evaporated under reduced pressure and water was added to the residue. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (3.7 g) as pale-yellow crystals.

Workup

  1. customThionyl chloride was evaporated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19662df896174a29bed4a0e5689a2135
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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