Ethanol → HCID 68560618, compound

HRID 1517323Notes

Reaction equation

C(O)C.[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13][C:14]#N)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[CH2:28](I)[CH:29](C)[CH3:30]>O>[CH2:14]([S:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH2:5][CH2:6]2)[CH:29]([CH3:30])[CH3:28]

Participants

Conditions

Temperature: 50 °C

Procedure

An ethanol (14 mL) solution of indolin-5-yl thiocyanate (compound described in the document J. Med. Chem., 1998, vol. 41, p. 1598; 1.33 g, 7.55 mmol) was added to a solution of sodium sulfide nonahydrate (1.84 g, 7.66 mmol) in water (2.8 mL), and the mixture was stirred at 50° C. for 2 hours. To the reaction solution, an ethanol (2.4 mL) solution of isobutyl iodide (1.2 mL, 10.4 mmol) was added, and the mixture was stirred at 50° C. for 2 hours. To the reaction solution, water was added, followed by extraction with ether three times. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-80:20-55:45, V/V) to obtain the title compound as brown oil (0.65 g, yield: 41%).

Workup

stirringthe mixture was stirred at 50° C. for 2 hours
extractionfollowed by extraction with ether three times
washThe obtained organic layer was washed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-80:20-55:45, V/V)

Sources & evidence

ORD record: ord-6164950c4d3f48f4aa1a2398d9f824f6
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232287B2

Reaction notes

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