Methyl Ethyl Ketone → HCID 14723557, compound

HRID 1646084Notes

Reaction equation

HRID 1646084 reaction equation
[SH:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][N:3]=1.[Br:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:14][CH2:15][CH2:16][CH2:17][S:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][N:3]=1

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178473173HCID 178473173, compound

Product 1

HCID 14723557HCID 14723557, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3 g of ethyl [(5-mercapto-1,3,4-thiadiazol-2-yl)thio]acetate, 9 g of 1,3-dibromopropane, 2.02 g of anhydrous potassium carbonate, 0.01 g of tetra-n-butylammonium bromide, and 20 ml of methyl ethyl ketone was vigorously stirred for 3 hours at 60° C. Toluene was added to the reaction mixture and the resultant mixture was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus formed was applied to silica gel column chromatography and eluted with a mixture of toluene and ethyl acetate (9:1) to provide 1.35 g of ethyl [[5-(3-bromopropyl)thio-1,3,4-thiadiazol-2-yl]thio]acetate.

Workup

  1. washthe resultant mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus formed
  5. washeluted with a mixture of toluene and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-715384734edc4b388968ccfc80eb46d4
Source dataset
uspto-grants-1993_01
Patent number
US05177215

Reaction notes

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