Hexane → 2-(Bis-methylsulfanyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo(5.2.1.0 1,5)dec-4-yl)-3-(2-vinyl-phenyl)-propan-1-one

HRID 2710

Reaction equation

[CH3:1][S:2][C:3]([S:22][CH3:23])=[N:4][CH2:5][C:6]([N:8]1[CH:12]2[CH2:13][CH:14]3[C:17]([CH3:19])([CH3:18])[C:11]2([CH2:16][CH2:15]3)[CH2:10][S:9]1(=[O:21])=[O:20])=[O:7].C([Li])CCC.CCCCCC.CN(P(N(C)C)(N(C)C)=O)C.I[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH:54]=[CH2:55]>O1CCCC1>[CH3:23][S:22][C:3]([S:2][CH3:1])=[N:4][CH:5]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH:54]=[CH2:55])[C:6]([N:8]1[CH:12]2[CH2:13][CH:14]3[C:17]([CH3:19])([CH3:18])[C:11]2([CH2:16][CH2:15]3)[CH2:10][S:9]1(=[O:20])=[O:21])=[O:7]

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve 2-(bis-methylsulfanyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-ethanone (7.91 g, 21.0 mmol) in tetrahydrofuran (100 mL) and cool to -78° C. Treat, by dropwise addition, with 1.6M n-butyllithium in hexane (13.1 mL, 21 mmol). Stir for 1.5 hours, then add hexamethylphosphotriamide (HMPA) (4.25 mL, 24.4 mmol). Stir for 15 minutes and add, via cannula, a solution of 1-iodomethyl-2-vinyl-benzene (6.1 g, 25 mmol) in tetrahydrofuran (100 mL). Stir overnight at room temperature, partition between saturated ammonium chloride (2×75 mL) and ethyl acetate (400 mL). Dry (Na2 SO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate) to give the title compound as a white solid (4.5 g).

Workup

stirringStir for 15 minutes
additionadd, via cannula
stirringStir overnight at room temperature
custompartition between saturated ammonium chloride (2×75 mL) and ethyl acetate (400 mL)
customDry (Na2 SO4)
custompurify by silica gel chromatography (2.5:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-e02594bc80d0495fbf7697482e3af45c
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731306

Linked notes

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