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

HRID 1656445Notes

Reaction equation

HRID 1656445 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), which is commercially available particularly from Aldrich, 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, 12.2 mmol) were added. The product precipitated after heating for 1/2 h 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 h, filtered and dried in a desiccator to give 28 g, 88% of 4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic 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-815be5cad7f945e18bc084d19bec97bc
Source dataset
uspto-grants-1993_10
Patent number
US05254573

Reaction notes

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