Acetic Acid → HCID 178467259, compound

HRID 1700639Notes

Reaction equation

HRID 1700639 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:15])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[CH2:8]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:31](O)(=[O:33])[CH3:32].Cl>CN(C)C1C=CN=CC=1.CN(C)C=O.O>[Cl:1][C:2]1[S:3][C:4]([Cl:15])=[CH:5][C:6]=1[CH:7]1[CH2:12][C:11](=[O:13])[C:10](=[C:31]([OH:33])[CH3:32])[C:9](=[O:14])[CH2:8]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 183175075-(2,5-Dichlorothiophen-3-yl)cyclohexane-1,3-dione

Product 1

HCID 178467259HCID 178467259, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2,5-dichlorothiophen-3-yl)cyclohexane-1,3-dione (3.07 g), 4-dimethylaminopyridine (2.14 g) and dicyclohexylcarbodiimide (3.13 g) in dimethylformamide (10 ml) was added acetic acid (1.26 g), and the mixture was stirred at room temperature for 13 hours. To the mixture were added water (30 ml) and 2N hydrochloric acid (10 ml), and the mixture was extracted with ethyl acetate. The organic layer was extracted with 0.5N sodium hydroxide solution, and to the aqueous layer was added 2N hydrochloric acid to make the solution acidic. The solution was extracted with ethyl acetate, and the organic layer was washed with water. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethyl acetate-hexane to give 5-(2,5-dichlorothiophen-3-yl)-2-(1-hydroxyethylidene)cyclohexane-1,3-dione (2.5 g) as yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe organic layer was extracted with 0.5N sodium hydroxide solution
  3. additionto the aqueous layer was added 2N hydrochloric acid
  4. extractionThe solution was extracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b29055eeb08649e9b933a737f9155c24
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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