Ethyl bromoacetate → HCID 19974176, compound

HRID 1587933Notes

Reaction equation

HRID 1587933 reaction equation
[H-].[Na+].[ClH:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][CH:15]([OH:22])[C:16]2[N:17]=[C:18]([CH3:21])[S:19][CH:20]=2)=[CH:7][CH:6]=1.Br[CH2:24][C:25]([O:27][CH2:28]C)=[O:26].C(=O)(O)[O-].[Na+]>CN(C)C=O>[ClH:3].[C:25]([CH2:24][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][CH:15]([OH:22])[C:16]2[N:17]=[C:18]([CH3:21])[S:19][CH:20]=2)=[CH:7][CH:6]=1)([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 19974113HCID 19974113, compound

Product 1

HCID 19974176HCID 19974176, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

100 mg (2.1 mmol) of Sodium hydride dispersion (50% in paraffin oil) are added to 280 mg (1 mmol) of N-[2-(4-hydroxyphenyl)ethyl]-2-hydroxy-2-(2-methyl-thiazol-4-yl)ethanamine hydrochloride dissolved in 7 ml of absolute dimethyl formamide. After stirring at room temperature for 15 minutes, the solution of 153 mg (1 mmol) of ethyl bromoacetate in 3 ml of absolute dimethylformamide is rapidly added dropwise. The mixture is then stirred overnight, 20 ml of saturated sodium bicarbonate solution are added, and extraction with methylene chloride is carried out. The extracts are dried, concentrated and, after dissolution in ether/methanol, the hydrochloride is precipitated with ethereal hydrochloric acid.

Workup

  1. stirringThe mixture is then stirred overnight
  2. extractionextraction with methylene chloride
  3. customThe extracts are dried
  4. concentrationconcentrated
  5. dissolutionafter dissolution in ether/methanol
  6. customthe hydrochloride is precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-df25e2fac01646b5a4c949cae74baf07
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

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