Hydrogen Peroxide → HCID 21986126, compound

HRID 28757Notes

Reaction equation

[CH:1]([C:3]1[CH2:4][CH:5]([CH2:9][C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)[CH2:6][CH2:7][CH:8]=1)=[CH2:2].NN.[OH2:17].OO>C(O)C>[CH2:1]([C:3]1[CH2:4][CH:5]([CH2:9][C:10]2[NH:11][C:12](=[O:17])[NH:13][CH:14]=2)[CH2:6][CH2:7][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of NiCl2 (0.364 g, 2.81 mmol) in EtOH (20 mL) was reacted with NaBH4 (0.053 mg, 1.40 mmol) at rt for 15 m after saturation of the solution with hydrogen gas. Ethylene diamine (0.17 g, 2.81 mmol) was added followed by the alkynyl imidazol (Intermediate R15, 0.26 g, 1.40 mmol) at rt for 45 m under an atmosphere of hydrogen gas. The mixture was filtered, diluted with chloroform and subjected to an aqueous work-up. The residue was purified by chromatography on SiO2 to give 4-(3-vinyl-cyclohex-3-enylmethyl)-1H-imidazole (72%). To 4-(3-vinyl-cyclohex-3-enylmethyl)-1H-imidazole (0.09 g, 0.47 mmol) in ethanol (3 mL) at 0° C. was added H2NNH2—H2O (0.93 mL, 19.1 mmol) followed by H2O2 (30%) (0.488 g, 14.4 mmol) and the mixture was stirred for 45 m at 0° C. and an additional 6 h at rt. The reaction was quenched and the material was purified by an aqueous work-up. The imidazole compound was purified further by isolation of the fumaric acid salt. The fumarate was converted to the compound 4-(3-ethyl-cyclohex-3-enylmethyl)-1,3-dihydro-imidazol-2-one (Compound 59) by the applicable step of Method P.

Workup

customThe reaction was quenched
customthe material was purified by an aqueous work-up
customThe imidazole compound was purified further by isolation of the fumaric acid salt

Sources & evidence

ORD record: ord-8a4c4576379c480cb7bf857715cf58d0
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419994B2

Reaction notes

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