1,2-Dichloroethane → N'1,N'3-dimethyl-N'1,N'3-di(phenylcarbonoselenoyl)malonohydrazide

HRID 420118Notes

Reaction equation

HRID 420118 reaction equation
[CH3:1][N:2]([C:4](=[Se:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:3].[C:12]([OH:18])(=O)[CH2:13][C:14](O)=[O:15].[CH2:19](Cl)[CH2:20]Cl>C(Cl)Cl>[CH3:1][N:2]([C:4]([C:20]1[CH:19]=[CH:7][CH:6]=[CH:5][CH:10]=1)=[Se:11])[NH:3][C:12](=[O:18])[CH2:13][C:14]([NH:3][N:2]([CH3:1])[C:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[Se:11])=[O:15]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 867Malonic AcidHCID 57551066N-methylbenzoselenohydrazide

Product 1

HCID 25052672N'1,N'3-dimethyl-N'1,N'3-di(phenylcarbonoselenoyl)malonohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-methylbenzoselenohydrazide (215 mg, 1.0 mmol) and malonic acid (53 mg, 0.5 mmol) in CH2Cl2 (5 mL), was added EDC (240 mg, 1.25 mmol). The mixture was stirred for 1 h at RT. The reaction mixture was diluted with CH2Cl2 (15 mL) and washed with water and brine. The organic layer was dried over MgSO4 and filtered. After removal of the solvent, the product was purified by chromatography column on silica gel (1:1 Hexane:EtOAc and EtOAc) and to give (N′1,N′3-dimethyl-N′1,N′3-di(phenylcarbonoselenoyl)malonohydrazide (Compound 1), 188 mg in 76% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customAfter removal of the solvent
  5. customthe product was purified by chromatography column on silica gel (1:1 Hexane:EtOAc and EtOAc)

Sources & evidence

ORD record
ord-cc8e0cfe5225427a83588063a4983b8d
Source dataset
uspto-grants-2012_01
Patent number
US08093425B2

Reaction notes

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