2-Chloroimidazoline sulfate → 2-[4-(5-Methoxythien-2-ylmethyl)phenyl]amino-imidazoline

HRID 723584Notes

Reaction equation

[CH3:1][O:2][C:3]1[S:7][C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(O)(O)(=O)=O.Cl[C:22]1[NH:23][CH2:24][CH2:25][N:26]=1>C(#N)C.ClCCl>[CH3:1][O:2][C:3]1[S:7][C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:22]3[NH:26][CH2:25][CH2:24][N:23]=3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of [4-(5-methoxythien-2-ylmethyl)-phenylamine (145 mg, 0.66 mmol) in acetonitrile (10 ml) was added 2-chloro-2-imidazoline sulfate (155 mg, 0.76 mmol) at 20–25° C. under nitrogen. The resulting suspension was heated at 80° C. for 1.5 hours. The mixture was diluted with dichloromethane and washed with 10% sodium hydroxide, water, dried (Na2SO4), and concentrated to dryness. Purification by preparative TLC, eluting with ethyl acetate/methyl alcohol/isopropylamine, gave 2-[4-(5-methoxythien-2-ylmethyl)phenyl]amino-imidazoline (132 mg, 70%) as a yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.12 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 6.39 (dt, J=3.7, 1.1 Hz, 1H), 5.98 (d, J=3.7 Hz, 1H), 3.92 (bs, 2H), 3.82 (S, 3H), 3.52 (S, 4H), 3.15–3.35 (broad, 2H).

Workup

washwashed with 10% sodium hydroxide, water
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness
customPurification by preparative TLC
washeluting with ethyl acetate/methyl alcohol/isopropylamine

Sources & evidence

ORD record: ord-7873e5ac97c44b5183d08e17adbbf1a1
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141584B2

Reaction notes

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