Methanol → 1-Methoxy-9H-thioxanthen-9-one

HRID 2373113Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([S:17][C:18]2[C:26](CC)=[C:25](CC)[CH:24]=[CH:23][C:19]=2[C:20](N)=[O:21])[CH:14]=[CH:15][CH:16]=1.CO>CCCCCCC.C1COCC1.O1CCCC1>[CH3:9][O:10][C:11]1[C:12]2[C:20](=[O:21])[C:19]3[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:17][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Finally, 1-methoxythioxanthen-9-one (S-12) was prepared. A stirred mixture of 2.05 mL of a 2.0 M solution in heptane/THF of lithium diisopropylamide (4.1 mmol) diluted with 15 mL of anhydrous tetrahydrofuran was cooled to 0° C. and treated dropwise with a solution of 2-[(3-methoxyphenyl)thio]diethylbenzamide (0.4 g, 1.4 mmol) in 3 mL of anhydrous tetrahydrofuran. The reaction mixture was warmed to ambient and stirred for 2 h. Methanol (1 mL) was added, and the resulting solution was washed twice with water, and then with brine. The solution was dried (Na2SO4) and the solvent was removed at reduced pressure to deposit a yellow solid. This crude product was recrystallized from methanol to provide 0.15 g (45% of theory) of a yellow solid. 1H NMR (CDCl3): δ 4.00 (s, 3H), 7.92 (d, 1H), 7.12 (d, 1H), 7.50 (m, 4H), 8.45 (d, 1H).

Workup

temperatureThe reaction mixture was warmed to ambient and
washthe resulting solution was washed twice with water
dry with materialThe solution was dried (Na2SO4)
customthe solvent was removed at reduced pressure
customThis crude product was recrystallized from methanol
customto provide 0.15 g (45% of theory) of a yellow solid

Sources & evidence

ORD record: ord-7793907239b74c3f82cb4ebbbb17d5b4
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459263B2

Reaction notes

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