Citric Acid → HCID 86645107, compound

HRID 658356Notes

Reaction equation

HRID 658356 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[CH3:10][N:11]([CH3:13])[NH2:12].C(N(CC)CC)C.C(O)(=O)[CH2:22][C:23](CC(O)=O)(C(O)=O)[OH:24]>C(#N)C>[CH2:23]([O:24][C:7](=[O:8])[CH2:3][C:4](=[O:5])[NH:12][N:11]([CH3:13])[CH3:10])[CH3:22]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 59761,1-DimethylhydrazineHCID 8471TriethylamineHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 86645107HCID 86645107, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl malonyl chloride (5.0 g, 33 mmol) was added to a mixed solution of N,N-dimethylhydrazine (4.0 g, 67 mmol), triethylamine (6.7 g, 66 mmol) and acetonitrile (30 mL) at 10° C. or below. The mixture was stirred overnight at room temperature. The reaction mixture was added with an aqueous solution of citric acid, and extracted with chloroform. The organic layer was washed with water, dried, and concentrated, to obtain 4.6 g of a desired product (yield: 79%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-12dab4fd81b14ff7801070fe52eea986
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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