Hydrochloric Acid → HCID 178508277, compound

HRID 1988784Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:13]C(=O)C)[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.Cl>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:13])[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 86 °C

Procedure

To a solution of acetylguaniidne (6.07 g, 60 mmol) in DMF (40 ml) was added a solution of 2-bromo-1-(3-bromo-phenyl)-ethanone in DMF (20 ml) dropwise at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction was taken into ethyl acetate and water. After separation, the organic layer was washed with brine, dried (MgSO4) and concentrated to give the crude product. The crude product was purified via flash column (silica gel, 3% methanol in chloroform with 0.3% NH4OH) to give N-[4-(3-bromo-phenyl)-1H-imidazol-2-yl]-acetamide as a white solid (2.03 g, 36% yield). The acetamide (1.5 g, 5.38 mmol) was dissolved in a solution of 40 ml methanol and 20 ml water. The concentrated hydrochloric acid was added slowly. The reaction was heated at 86° C. for 4 hours. The reaction was concentrated to provide the HCI salt of 4-(3-bromo-phenyl)-1H-imidazol-2-ylamine (1.276 g, 86% yield). LC/MS (m/z 2378.05, 240.06 (M+H)+); HPLC Rt: 1.86 min.

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-74ad6df3dfce4b2e90cf1973fc3be5ac
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642273B2

Reaction notes

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