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

HRID 2255293Notes

Reaction equation

HRID 2255293 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=N)=[CH:6][CH:5]=1.C[N:14](C=O)C.[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[NH2:14][N:10]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([NH:3][C:18](=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 756264-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

4-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 0.012 mmol) were added. The product precipitated 20 after heating for 1/2h at 100° C. The product was filtered, washed with water, acetonitrile and ether. The light 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-oxo-butanoic acid as a white yellow solid which decomposes between 270° and 290° C.

Workup

  1. additionwere added
  2. customThe product precipitated 20
  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-a9efc5017b4a4d2a89933a815d532982
Source dataset
uspto-grants-1993_08
Patent number
US05239113

Reaction notes

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