Potassium tert-butoxide → HCID 58638684, compound

HRID 1591759Notes

Reaction equation

HRID 1591759 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([N:18]([CH2:20][CH2:21][N:22]([CH2:36][CH2:37][CH2:38]Cl)[C:23]([NH:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)=[O:24])[CH3:19])(=[O:17])=[O:16]>CN(C)C=O>[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([N:18]([CH2:20][CH2:21][N:22]1[CH2:36][CH2:37][CH2:38][N:25]([CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[CH:32][CH:33]=2)[C:23]1=[O:24])[CH3:19])(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58638727HCID 58638727, compound

Product 1

HCID 58638684HCID 58638684, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

31 mg (0.28 mmol) of potassium tert.-butoxide were added to a solution of 0.147 g (0.28 mmol) of 2,3-dichloro-N-(2-{1-(3-chloropropyl)-3-[2-(4-cyanophenyl)-ethyl]ureido}ethyl)-N-methylbenzenesulphonamide in 8 ml of dimethylformamide, and the mixture was stirred at room temperature for 24 hours. The mixture was then evaporated to dryness. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic extracts were washed with water, saturated sodium hydrogen sulphate solution and saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: dichloromethane/ethanol 40:1).

Workup

  1. customThe mixture was then evaporated to dryness
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic extracts were washed with water, saturated sodium hydrogen sulphate solution and saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-23485afe7eb7449e8903d24ecdd15059
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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