Dimethyl Sulfoxide → HCID 12451263, compound

HRID 572622Notes

Reaction equation

HRID 572622 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:13])[CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:14](=S)=[S:15].[H-].[Na+].CI.[CH3:21][S:22]([CH3:24])=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[C:9]([C:10](=[C:21]([S:15][CH3:14])[S:22][CH3:24])[C:11]#[N:12])=[O:13]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 27580633-(3,4-Dichlorophenyl)-3-oxopropanenitrile

Product 1

HCID 12451263HCID 12451263, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(3,4-dichlorophenyl)-3-oxopropanenitrile (3.3 g, 15.4 mmol) and carbon disulfide (0.927 mL, 15.4 mmol) in DMSO (50 mL) under an atmosphere of argon at 15° C. was added sodium hydride (0.856 g, 033.9 mmol) with vigorous stirring. The reaction mixture was stirred at this temperature for 10 min and was allowed to warm to rt. To the reaction mixture was added methyl iodide (1.92 mL, 30.8 mmol) and the mixture was stirred at rt for 30 min. The reaction mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography to give 2-(3,4-dichlorobenzoyl)-3,3-bis(methylsulfanyl)acrylonitrile (2.9 g, 59%). LCMS: (FA) ES-318.1. 1H NMR (400 MHz, CDCl3) δ: 7.95 (d, 1H), 7.73 (dd, 1H), 7.56 (d, 1H), 2.82 (s, 3H) and 2.55 (s, 3H).

Workup

  1. stirringthe mixture was stirred at rt for 30 min
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f077281237ad4d9c910411a628761627
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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