Hydrochloric Acid → 2-[1-(2-chloro-3-ethynyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole

HRID 1254974Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].CO[C:7](=N)[CH:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[C:13]=1[Cl:20])[CH2:9][CH3:10].Cl>C(O)C>[Cl:20][C:13]1[C:14]([C:18]#[CH:19])=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH:8]([C:7]1[NH:3][CH2:2][CH2:1][N:4]=1)[CH2:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethylene diamine (30 mg, 0.5 mmol) was dissolved in dry ethanol (1.9 ml). The solution was cooled to 0° C. and 2-(2-chloro-3-ethynyl-phenoxy)-butyrimidic acid methyl ester (100 mg, 0.4 mmol) was added. After 1 h a solution of concentrated HCl (few drops) in ethanol (0.9 ml) was added and the reaction mixture was stored overnight at 0° C. The reaction mixture was then diluted with a further portion of ethanol (1.6 ml) and heated to 75° C. for 5 h. After cooling to room temperature a precipitate was formed that was filtered and discarded. The filtrate was evaporated and treated with CHCl3. Another precipitate was formed, which was filtered again. Finally, the CHCl3 phase was evaporated to yield 2-[1-(2-chloro-3-ethynyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole; 1H-NMR (CDCl3) 1.08 t, 3H, 1.9-2.1 m, 2H, 3.10-3.9, vbr s, 4H, 3.39, s, 1H, 4.85 dd, 1H, 7.05 d, 1H, 7.1-7.2, m, 2H.

Workup

temperatureheated to 75° C. for 5 h
temperatureAfter cooling to room temperature a precipitate
customwas formed
filtrationthat was filtered
customThe filtrate was evaporated
additiontreated with CHCl3
customAnother precipitate was formed
filtrationwhich was filtered again
customFinally, the CHCl3 phase was evaporated

Sources & evidence

ORD record: ord-324c5c8a89c442fa8a9e43fa85c8e203
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455663B2

Reaction notes

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