2-Methoxyphenethylamine → HCID 19704106, compound

HRID 2257784Notes

Reaction equation

HRID 2257784 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2].[CH3:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1CCN>C(#N)C>[CH3:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:11][CH2:12][NH:8][C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2]

Participants

4

Reactant 2

HCID 748962-MethoxyphenethylamineHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 19704106HCID 19704106, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1'-thiocarbonyldiimidazole (1.78 g, 10 mmol) and 2-methoxyphenethylamine (1.51 g, 10 mmol) in acetonitrile 25 mL) was stirred at room temperature for 20 h. The resulting precipitate was collected by filtration to provide 1.40 g (53%) of the titled product: IR (KBr, cm-1) 2944, 1563, 1493, 1409, 1282, 1246, 1031, 755; 1H NMR (300 MHz, DMSO-d6) δ 12.0 (br s, 1H), 7.65 (s, 1H), 7.25 (m, 2H), 7.05-6.9 (m, 4H), 3.8 (m, 2H), 3.8 (s, 3H), 2.95 (t, J=7 Hz, 2H); MS (FD) m/e 261 (M+); UV (EtOH) 278 nm (ε=7083), 216 nm (ε=12683), 203 nm (ε=22221).

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e604265519d143ec833e0271db44f01b
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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