Stannous chloride dihydrate → 5-Methoxy-9H-thioxanthen-2-ylamine

HRID 1825782Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[S:5][C:6]1[CH:7]=[CH:8][C:9]([N+:17]([O-])=O)=[CH:10][C:11]=1[CH2:12]2.O.O.Cl[Sn]Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[S:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:17])=[CH:10][C:11]=1[CH2:12]2

Participants

Conditions

Temperature: 50 °C

Procedure

5-Methoxy-2-nitro 9H-thioxanthene (11.59 g, 42.40 mmol) was suspended in ethyl acetate (250 ml). SnCl2.2H2O (47.84 g, 212 mmol) was added and the clear yellow solution was stirred at 50° C. overnight. The reaction was the quenched with NaOH (2M) and then extracted with ethyl acetate (3×300 ml). The organics were washed with saturated brine (100 ml), dried over magnesium sulphate and the solvents were removed in vacuo to give the title compound (10.32 g, 100%) as viscous yellow oil. The oil was used without further purification. 1HNMR (300 MHz, DMSO-d6): δH=3.83 (3H, s), 3.67 (2H, s), 5.14 (2H, bs), 6.43 (1H, dd), 6.61 (1H, d), 6.89 (1H, d), 6.99 (1H, d), 7.06 (1H, d), 7.18 (1H, t). m/z (LC-MS, ESP), RT=3.88 min, (M++1)=244.

Workup

customquenched with NaOH (2M)
extractionextracted with ethyl acetate (3×300 ml)
washThe organics were washed with saturated brine (100 ml)
dry with materialdried over magnesium sulphate
customthe solvents were removed in vacuo

Sources & evidence

ORD record: ord-c691f7cc4efd4f4494afb438195bf4cc
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049313B2

Reaction notes

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