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

HRID 1419550Notes

Reaction equation

Cl.Cl.NC1C=CC=CC=1C(N)=N.CN(C=O)C.C1(=O)OC(=O)CC1.Cl.[NH2:26][N:27]=[CH:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:42])[CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:31][CH:30]=1>N1C=CC=CC=1>[NH2:26][N:27]=[CH:28][C:29]1[CH:30]=[CH:31][C:32]([NH:35][C:36](=[O:42])[CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Aminobenzamidine di-HCl (25 g, 120 mmol), which is commercially available from Aldrich, was added to dry DMF (100 mL). To this was added dry pyridine (100 mL) and succinic anhydride (12 g, 120 mmol) followed by N,N-dimethylaminopyridine (DMAP, 0.15 g). The product precipitated after heating for 0.5 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 stirred for 1 hour, filtered and dried in a desiccator to give 28 g, 88% isolated yield of a yellowish-white solid whose nmr and mass spectra is consistent with 4-[[4-(aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid HCl salt. Mp: 270°-290° C., decomp.

Workup

customThe product precipitated
filtrationThe product was filtered
washwashed with water, acetonitrile and ether
addition4N HCl in dioxane (100 mL) was added
filtrationfiltered
customdried in a desiccator
customto give 28 g, 88%
customisolated yield of a yellowish-white solid whose nmr

Sources & evidence

ORD record: ord-227858a5c1974921954c2fc72a650d88
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886208

Reaction notes

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