Potassium Carbonate → HCID 19003511, compound

HRID 2259408Notes

Reaction equation

HRID 2259408 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[CH:7][S:8](=O)[C:4]=2[CH:3]=1.Cl.[CH3:13][N:14]([CH2:16][CH2:17]Cl)[CH3:15].C([O-])([O-])=[O:20].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH2:17][CH2:16][N:14]([CH3:15])[CH3:13])[C:7](=[O:20])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 53400706HCID 53400706, compound

Product 1

HCID 19003511HCID 19003511, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound (VIII) (9.28 g, 50 mmol), N,N-dimethylaminoethylchloride hydrochloride (XIe) (7.92 g, 55 mmol), and K2CO3 (16.58 g, 120 mmol) in acetone (93 ml) was refluxed for 20 hours with stirring. After the reaction was complete, the reaction mixture was concentrated in vacuo. The residue was extracted with ethyl acetate. The layer of ethyl acetate was dried over MgSO4 and subjected to column chromatography on silica gel. From the eluate eluted with ethyl acetate, compound (XIIe) (3.3 g, yield=64.3%) was obtained as an oil.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. dry with materialThe layer of ethyl acetate was dried over MgSO4
  4. washFrom the eluate eluted with ethyl acetate
  5. customcompound (XIIe) (3.3 g, yield=64.3%) was obtained as an oil

Sources & evidence

ORD record
ord-a73c1ec75485464f9cbdd007ed6a02cf
Source dataset
uspto-grants-1995_12
Patent number
US05473066

Reaction notes

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