Benzylhydrazine dihydrochloride → HCID 178515600, compound

HRID 2266301Notes

Reaction equation

HRID 2266301 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). HPLC/MS (method A): retention time=3.29 min, (M+H)+=313.1. 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-9c864979b3224d53a3c3f3886cd0b8a4
Source dataset
uspto-grants-2010_12
Patent number
US07858639B2

Reaction notes

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