Acetohydrazide → 1-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid N'-acetyl-hydrazide

HRID 2266408Notes

Reaction equation

HRID 2266408 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:16]([NH:19][NH2:20])(=[O:18])[CH3:17].ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:16]([NH:19][NH:20][C:13]([C:11]1[N:10]=[CH:9][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH:12]=1)=[O:15])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 234449541-(3-Bromophenyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 577508851-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid N'-acetyl-hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5 (0.30 g, 1.1 mmol), acethydrazide (82 mg, 1.1 mmol) diisopropylethyl amine (975 uL, 5.6 mmol), and 1-hydroxy-7-azabenzotriazole (HOAt, 177 mg, 1.3 mmol) in DMF (10 mL) was added and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (EDC HCl; 249 mg, 1.3 mmol). The mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue was extracted with hot ethyl acetate. The solvent was evaporated and crystallised from MeOH to give the title compound.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with hot ethyl acetate
  3. customThe solvent was evaporated
  4. customcrystallised from MeOH

Sources & evidence

ORD record
ord-8b1f7fafd1764298ab31abdea735702f
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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