Potassium Carbonate → HCID 18317543, compound

HRID 1700645Notes

Reaction equation

HRID 1700645 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:27])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11]([NH:13][NH:14]S(C2C=CC(OC)=CC=2)(=O)=O)=[CH:10][C:9](=[O:26])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36](=O)[CH2:37][CH3:38]>CO>[Cl:1][C:2]1[S:3][C:4]([Cl:27])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11]2[N:13]=[N:14][CH:35]=[C:36]([CH2:37][CH3:38])[C:10]=2[C:9](=[O:26])[CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 131561-Bromo-2-butanoneHCID 18317474HCID 18317474, compound

Product 1

HCID 18317543HCID 18317543, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-(2,5-dichlorothiophen-3-yl)-1-[2-(4-methoxyphenylsulfonyl)hydrazino]cyclohexen-3-one (1.79 g), anhydrous potassium carbonate (0.718 g) and methanol (30 ml) was added under ice-cooling 1-bromobutan-2-one (0.785 g), and the mixture was stirred at room temperature for 2 hours. To the mixture was added anhydrous potassium carbonate (1.2 g), and the mixture was stirred for 2 hours. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified with silica gel column chromatography to give 7-(2,5-dichlorothiophen-3-yl)-4-ethyl-5,6,7,8-tetrahydrocinnolin-5-one (0.26 g) as oil.

Workup

  1. additionwas added under ice-
  2. stirringthe mixture was stirred for 2 hours
  3. customUnder reduced pressure, the solvent was evaporated
  4. extractionthe residue was extracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-22768802bf7a4176abc1d327e458e543
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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