Dimethyl Sulfoxide → 1-(2-Methoxy-6-((4-methoxybenzyl)oxy)phenyl)-3,3-bis(methylthio)prop-2-en-1-one

HRID 1878309Notes

Reaction equation

HRID 1878309 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:6]=1[C:21](=[O:23])[CH3:22].[C:24](=S)=[S:25].CI.[CH3:29][S:30]([CH3:32])=O>O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:6]=1[C:21](=[O:23])[CH:22]=[C:29]([S:25][CH3:24])[S:30][CH3:32]

Participants

7

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 56973356HCID 56973356, compound

Product 1

HCID 583058241-(2-Methoxy-6-((4-methoxybenzyl)oxy)phenyl)-3,3-bis(methylthio)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 mL round bottom flask is charged with 95% NaH (7.28 g, 288 mmol) and dry DMSO is added (170 mL). To the resulting heterogeneous mixture is added dropwise, 1-[2-methoxy-6-(4-methoxybenzyloxy)phenyl]ethanone (41.2 g, 144 mmol) in dry DMSO (60 mL). The mixture is stirred at room temperature for 10 min, at which time carbon disulfide is added dropwise (8.69 mL, 144 mmol), followed immediately by methyl iodide (18.0 mL, 288 mmol). Heat and gas are evolved during the addition of both reagents prompting careful addition. The homogenous solution is stirred for 18 h at room temperature and then poured slowly into three volumes of water. The solid product is filtered and dried under high vacuum to give the title compound as an orange solid.

Workup

  1. additionis added (170 mL)
  2. additionTo the resulting heterogeneous mixture is added dropwise
  3. additionis added dropwise (8.69 mL, 144 mmol)
  4. temperatureHeat
  5. additiongas are evolved during the addition of both reagents
  6. additionaddition
  7. filtrationThe solid product is filtered
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-26d7856fa1de487382322a78168d590c
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

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