4,5-dihydro-1H-imidazole-2-sulfonic acid → 2-(trans-2-Ethylcyclohexylamino)-2-imidazoline

HRID 654283Notes

Reaction equation

Cl.[CH2:2]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH2:10])[CH3:3].[NH:11]1[CH2:15][CH2:14][N:13]=[C:12]1S(O)(=O)=O>C(O)C(C)C>[CH2:2]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][C:12]1[NH:13][CH2:14][CH2:15][N:11]=1)[CH3:3]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of trans-2-ethylcyclohexylamine hydrochloride (0.30 g, 2.36 mmol), imidazoline-2-sulfonic acid (0.704 g, 4.72 mmol) and isobutanol (3 ml) was heated to 125° C. and maintained at that temperature for 2 hours. The mixture was cooled to room temperature, concentrated in vacuo and chromatographed (silica gel, 3:1 CHCl3 /CH3OH saturated with NH3 (g)) to yield 0.253 g (a yield of 65%) of the title compound as a white solid, which was characterized spectroscopically.

Workup

temperaturemaintained at that temperature for 2 hours
temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo
customchromatographed (silica gel, 3:1 CHCl3 /CH3OH saturated with NH3 (g))

Sources & evidence

ORD record: ord-06633e46418b4ffbbd751cefa9a63344
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130441

Reaction notes

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