2-(Ethylamino)ethanol → HCID 68470062, compound

HRID 504985Notes

Reaction equation

HRID 504985 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([NH:9][CH2:10][CH2:11][OH:12])C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O>[CH3:7][N:9]([CH3:2])[CH2:10][CH2:11][OH:12].[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Conditions

Temperature
80 °C

Procedure

2-Bromothiophene (16.3 g, 0.1 mol), 2-(ethylamino)ethanol (100 ml), Cu metal (0.32 g), CuI (0.85 g), K3PO4(42.4 g) were added to a flask fitted with a magnetic stir bar, a condenser and sealed with a septum. The reaction mixture was stirred at 80° C. for 72 hour under nitrogen position pressure. After the reaction cooled to room temperature, 600 ml water was added and mixture was extracted with ethyl ether (3*200 ml). The combined organic layers were then washed with brine and dried over MgSO4. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel eluted with hexane/EtoAc (1:1). The product was obtained as a liquid. Examples of Amination of 2-bromothiophene are shown in Table 7.

Workup

  1. customfitted with a magnetic stir bar, a condenser
  2. customsealed with a septum
  3. temperatureAfter the reaction cooled to room temperature
  4. extractionmixture was extracted with ethyl ether (3*200 ml)
  5. washThe combined organic layers were then washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography on silica gel
  9. washeluted with hexane/EtoAc (1:1)
  10. customThe product was obtained as a liquid

Sources & evidence

ORD record
ord-88a78813709d44459b35f15ed7c54712
Source dataset
uspto-grants-2010_08
Patent number
US07781187B2

Reaction notes

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