Benzylhydrazine dihydrochloride → HCID 178515600, compound

HRID 2250341Notes

Reaction equation

HRID 2250341 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:14])O[C:11](=[O:13])[CH:12]=2)=[CH:4][CH:3]=1.Cl.Cl.[CH2:17]([NH:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(=O)C>[CH2:17]([N:24]1[C:11](=[O:13])[CH:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]([OH:14])=[N:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 146540Benzylhydrazine dihydrochlorideHCID 5859973-(4-Chlorophenyl)-2,5-furandione

Product 1

HCID 178515600HCID 178515600, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 3-(4-chlorophenyl)-2,5-furandione (10.24 g, 66.9 mmol) in acetic acid (300 mL) was added benzylhydrazine dihydrochloride in one portion (19.6 g, 100 mmol). The reaction mixture was stirred at reflux for 14 h. Analysis by HPLC/MS indicated the reaction was complete. After cooling to room temperature, the resulting white suspension was filtered. The collected solid was washed with EtOAc (20 mL×2), and dried in a 50° C. vacuum oven for 16 h to yield 6.5 g of the desired product as a white solid. The filtrate was concentrated under reduced pressure, and the obtained residue was crystallized in EtOAc to afford additional 1.6 g of the title compound (8.1 g in total, 39% yield). LC/MS (method A): retention time=3.30 min, (M+H)+=313. 1H NMR (DMSO-d6, 500 MHz): δ 11.62 (s, 1H), 7.65 (d,J=10 Hz, , 2H), 7.51 (d,J=10 Hz, 2H), 7.23-7.38 (m, 5H), 7.04 (s, 1H), 5.11 (s, 2H).

Workup

  1. temperatureat reflux for 14 h
  2. filtrationthe resulting white suspension was filtered
  3. washThe collected solid was washed with EtOAc (20 mL×2)
  4. customdried in a 50° C. vacuum oven for 16 h

Sources & evidence

ORD record
ord-25d6d7d5ed26419c9d3e577a49c12586
Source dataset
uspto-grants-2008_01
Patent number
US07317012B2

Reaction notes

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