Dimethyl Sulfoxide → HCID 53842401, compound

HRID 910103Notes

Reaction equation

HRID 910103 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11]Cl)[C:5]=2[O:4][CH2:3][CH2:2]1.[C-:13]#[N:14].[Na+].CS(C)=O>C(OCC)(=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][C:13]#[N:14])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 224188622-AMino-N-(2,3-dihydro-benzo[1,4]dioxin-6-ylMethyl)-acetaMide

Product 1

HCID 53842401HCID 53842401, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Add (2,3-Dihydrobenzo[1,4]dioxin-5-yl)chloromethane (1.9 g, 10.2 mmol) and sodium cyanide (655 mgs, 13.3 mmol) to dimethylsulfoxide (20 mL). Stir under nitrogen at 65° C. for 18 hours. Dilute the reaction with ethyl acetate, wash with 0.1 molar aqueous sodium carbonate and aqueous saturated sodium chloride. Dry the organic phase over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from neat hexane to 50% ethyl acetate in hexane to obtain 1.23 g (68%) of the desired compound as a white solid.

Workup

  1. additionDilute
  2. washwash with 0.1 molar aqueous sodium carbonate and aqueous saturated sodium chloride
  3. dry with materialDry the organic phase over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-2e1e993b9fdc48759885201e6a95d854
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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