Carbon Disulfide → 3-(1,3-dithian-2-ylidene)pentane-2,4-dione

HRID 1829724Notes

Reaction equation

HRID 1829724 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].C(=O)([O-])[O-].[K+].[K+].[C:14](=[S:16])=[S:15].Br[CH2:18][CH2:19][CH2:20]Br>CN(C)C=O>[S:15]1[CH2:20][CH2:19][CH2:18][S:16][C:14]1=[C:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 6819943-(1,3-dithian-2-ylidene)pentane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-pentanedione (10.5 ml) in dimethylformamide (200 ml) was added potassium carbonate (42.5 g) then carbon disulfide (9.3 ml). To the resulting mixture was added 1,3-dibromopropane, dropwise over 40 min. The mixture was stirred at ambient temperature under a nitrogen atmosphere for 20 hrs. then ice/water (200 ml) was added and the suspension was stirred for 1 hr. The solid was collected by filtration, washed with water and then recrystallised from ethanol to give the sub-title compound as a solid (23.3 g).

Workup

  1. stirringthe suspension was stirred for 1 hr
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4a3baaa74266419bbcad0d5fb64e3d27
Source dataset
uspto-grants-2006_06
Patent number
US07064126B2

Reaction notes

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