Dimethylformamide → 2-(3-Chloropropylsulfanyl)thiophene

HRID 1792499Notes

Reaction equation

HRID 1792499 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[SH:11].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[Cl:5][CH2:4][CH2:3][CH2:2][S:11][C:7]1[S:6][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 5226742-Thiophenethiol

Product 1

HCID 220310762-(3-Chloropropylsulfanyl)thiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.7 mL 1-bromo-3-chloropropane was added to a mixture of 2 mL thiophen-2-thiol, 5.86 g potassium carbonate and 40 mL N,N-dimethylformamide under ice-cooling and then stirred at room temperature for 2 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed with water plus brine (×2) and then with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was purified by silica gel column chromatography (hexane) to give 4.19 g of the title compound as a pale yellow oil.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washwashed with water plus brine (×2)
  4. dry with materialwith brine and dried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated
  7. customThe resulting residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-e61ef03a6a7048389b3fabfde9a97bb5
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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