4-(5-Isopropoxythien-2-ylmethyl)-phenylamine → 2-[4-(5-Isopropoxythien-2-ylmethyl)phenyl]amino-imidazoline

HRID 634831Notes

Reaction equation

[CH:1]([O:4][C:5]1[S:9][C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].S(O)(O)(=O)=O.Cl[C:24]1[NH:25][CH2:26][CH2:27][N:28]=1>ClCCl>[CH:1]([O:4][C:5]1[S:9][C:8]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:24]3[NH:28][CH2:27][CH2:26][N:25]=3)=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(5-isopropoxythien-2-ylmethyl)-phenylamine (131 mg, 0.53 mmol) in aceonitrile (8 ml) was added 2-chloro-2-imidazoline sulfate (121 mg, 0.59 mmol) at 20-25° C. under argon. The mixture was heated at 80° C. for 1.5 hours. The mixture was diluted with dichloromethane and washed with sodium hydroxide, water, dried (Na2SO4) and concentrated to dryness. Purification by preparative TLC, eluting with ethyl acetate/methyl alcohol/isopropylamine, gave 2-[4-(5-isopropoxythien-2-ylmethyl)phenyl]amino-imidazoline (150 mg, 90%) as a thick yellow oil; 1H NMR (300 Mhz, CDCl3δ 7.13 (d,J=8.4 Hz, 2H) 6.93 (d,J=8.4 Hz, 2H), 6.37 (dt, J=3.7, 1.0 Hz, 1H), 6.02 (d, J=3.7 Hz, 1H), 4.28 (quintet, J=6.2 Hz, 1H), 3.93 (bs, 2H), 3.52 (5, 4H), 3.24-3.5 (broad, 2H), 1.32 (d, J=6.2 Hz, 6H). MS m/e (%):316 (M+1, 100%).

Workup

washwashed with 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-99be7fe422c94a0fb1be468ce518361c
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184242B2

Reaction notes

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