Potassium Carbonate → HCID 16778897, compound

HRID 334521Notes

Reaction equation

HRID 334521 reaction equation
ClC1C=C(C=C(Cl)C=1)C(NN)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[C:17]([NH:19][NH:20][C:21](=[O:24])[CH2:22][Cl:23])=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:23][CH2:22][C:21]1[O:24][C:17]([C:16]2[CH:15]=[C:14]([Cl:13])[CH:27]=[C:26]([Cl:28])[CH:25]=2)=[N:19][N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27359663,5-dichlorobenzohydrazideHCID 13365860HCID 13365860, compound

Product 1

HCID 16778897HCID 16778897, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 5 (700 mg, 2.14 mmol), compound 6 (222 mg, 1.86 mmol) and K2CO3 (772 mg, 5.59 mmol, 2 eq.) in 10 ml of DMF was heated to 100° C. for 3 hours. The reaction mixture was brought to ambient temperature, filtered and the filtrate was evaporated to obtain a crude residue which was purified by column chromatography using EtOAc/hexane (50:50) as an eluent to obtain compound 7 as a colorless liquid (340 mg). Yield: 50%.

Workup

  1. customwas brought to ambient temperature
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customto obtain a crude residue which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1092bc6835c04968a7e0e0bc79cae3ab
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Reaction notes

Loading…