Water → 2-(Ethylamino)-4-thiazoleethanol

HRID 1369204Notes

Reaction equation

HRID 1369204 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17](OCC)=[O:18])[N:15]=1)(=O)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][OH:18])[N:15]=1)[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3477732Ethyl 2-acetylamino-4-thiazoleacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 120714692-(Ethylamino)-4-thiazoleethanolYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1.0 M LiAlH4 in THF (179 mL, 179 mmole) was added dropwise a solution of ethyl 2-acetylamino-4-thiazoleacetate (4.4 g, 17.9 mmole) in THF (50 mL). After complete addition, the reaction mixture was heated at reflux for 3 hr, then was worked up by sequential addition of H2O (0.7 mL), 10% NaOH (0.7 mL), and H2O (2.1 mL). The resulting mixture was filtered through celite® and the filtrate was concentrated. Purification by flash chromatography on silica gel (5% MeOH/CH2H2) gave the title compound (1.6 g, 53%) as an amber oil: MS (ES) m/e 173 (M+H)+.

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 3 hr
  4. filtrationThe resulting mixture was filtered through celite®
  5. concentrationthe filtrate was concentrated
  6. customPurification by flash chromatography on silica gel (5% MeOH/CH2H2)

Sources & evidence

ORD record
ord-791195f9e67b4f65be03af2deeed334d
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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