Dimethylformamide → 4-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid

HRID 1636900Notes

Reaction equation

HRID 1636900 reaction equation
Cl.Cl.N[C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=N.C[N:14]([CH:16]=[O:17])C.[C:18]1(=[O:24])[O:23]C(=O)[CH2:20][CH2:19]1.C[N:26](C1C=CC=CN=1)C>N1C=CC=CC=1>[NH2:26][N:8]=[CH:6][C:5]1[CH:4]=[CH:12][C:11]([NH:14][C:16](=[O:17])[CH2:20][CH2:19][C:18]([OH:23])=[O:24])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 669893132-Aminobenzamidine dihydrochloride

Product 1

HCID 699510564-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Aminobenzamidine di-HCl (25 g, 120 mmol) was added to dry DMF (100 ml). To this solution dry pyridine (100 ml) and succinic anhydride (12 g, 120 mmol) followed by dimethylaminopyridine (DMAP, 1.5 g, 0.012 mmol) were added. The product precipitated after heating for 1/2 hour at 100° C. The product was filtered, washed with water, acetonitrile and ether. The white solid was suspended in dioxane, 4N HCl in dioxane (100 ml) was added and the suspension was stirred for 1 hour, filtered and dried in a desiccator to give 28 g, 88% of 4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxo-butanoic acid as a white yellow solid which decomposes between 270 and 290° C.

Workup

  1. additionwere added
  2. customThe product precipitated
  3. filtrationThe product was filtered
  4. washwashed with water, acetonitrile and ether
  5. addition4N HCl in dioxane (100 ml) was added
  6. filtrationfiltered
  7. customdried in a desiccator

Sources & evidence

ORD record
ord-97d4a19fb87f44f1935270edfe41574f
Source dataset
uspto-grants-2000_03
Patent number
US06037365

Reaction notes

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