Hydrochloric Acid → N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide

HRID 722410

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].CCN(C(C)C)C(C)C.Cl.[NH2:31][CH2:32][CH2:33][C:34]([NH2:36])=[O:35].Cl>C(#N)C>[C:34]([CH2:33][CH2:32][NH:31][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])(=[O:35])[NH2:36]

Participants

Conditions

Temperature: 80 °C

Procedure

N-(4-fluoro-3-nitro-phenyl)-N-methyl-benzamide (1.47 g, 5.37 mmol) was taken up in dry acetonitrile under argon, DIEA (2.08 g, 16.11 mmol, 2.80 ml) and β-alanine amide hydrochloride (1.00 g, 8.06 mmol) were added. The reaction mixture was heated to 80° C. for 48 h. The reaction was poured into 1N HCl and the aqueous layer was extracted 3× with ethyl acetate. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The residue was triturated twice with cold hexane and dried to give N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide. (1.75 g, 95%)

Workup

extractionthe aqueous layer was extracted 3× with ethyl acetate
washThe combined organic layers were washed with water, brine
dry with materialdried over magnesium sulfate
filtrationThe solution was filtered
customthe solvent removed under reduced pressure
customThe residue was triturated twice with cold hexane
customdried

Sources & evidence

ORD record: ord-e834417c845e47c1acbbc78398a6df70
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138420B2

Linked notes

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