Diethylamine → 5-(Diethylamino)thiophene-2-carbaldehyde

HRID 1663265Notes

Reaction equation

HRID 1663265 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10]>O>[CH2:9]([N:11]([CH2:12][CH3:13])[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1)[CH3:10]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 153969095-(Diethylamino)thiophene-2-carbaldehydeYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round flask (100 mL) was added 5-bromothiophene-2-carboxaldehyde (1.37 mL) in 15 mL of distilled water. Diethylamine (12 mL) was added slowly, followed by refluxing for six days. Purification by flash chromatography provided the title compound as a brownish oil (1.13 g, 54%). 1H-NMR (300 MHz, [D] acetone): δ=9.46 (s, 1H), 7.56 (d, 1H, 3J=4.4 Hz), 6.07 (d, 1H, 3J=4.4 Hz), 3.485 (q, 4H, 3J=7.1 Hz), 1.23 (t, 6H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=179.2, 166.0, 140.8, 125.9, 102.8, 47.6, 11.8.

Workup

  1. temperatureby refluxing for six days
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-fdb2201a504547968ca7853d41b00f58
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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