Dimethyl Sulfoxide → HCID 18331406, compound

HRID 2270555Notes

Reaction equation

HRID 2270555 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:8][C:9]=1[CH2:10][CH3:11])#[N:2].Cl[CH2:16][C:17]1[C:18]([CH2:23]Cl)=[CH:19][CH:20]=[CH:21][CH:22]=1.CS(C)=O.CC(C)([O-])C.[K+]>O.C(OCC)(=O)C>[C:1]([C:3]1([C:4]2[CH:5]=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:8][C:9]=2[CH2:10][CH3:11])[CH2:23][C:18]2[C:17](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16]1)#[N:2]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 119191,2-Bis(chloromethyl)benzeneHCID 18331423HCID 18331423, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18331406HCID 18331406, compoundYield 29.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the compound (3.0 g) obtained in Example 25a, α,α′-dichloro-o-xylene (4.15 g) and dimethyl sulfoxide (200 ml), potassium t-butoxide (3.55 g) was added and after stirring the resulting mixture at room temperature for 3 h, ethyl acetate and water were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (1.36 g) (yield, 29%).

Workup

  1. additionwas added
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2bd456b6dab432a94fc205a2712695d
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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