Sodium Hydroxide → HCID 18422993, compound

HRID 1282186Notes

Reaction equation

HRID 1282186 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:15]N1C(=O)CCC1=O.[OH-].[Na+]>C(O)(=O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[S:11][C:12]([Br:15])=[CH:13][N:14]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 18423162HCID 18423162, compound

Product 1

HCID 18422993HCID 18422993, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-acetyl-1-(thiazol-2-yl)piperazine (3.1 g) and N-bromosuccinimide (2.9 g) in acetic acid (14 ml) was stirred at room temperature for 1 hr. The reaction mixture was neutralized with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-brown solid (2.9 g). The obtained pale-brown solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1) to give the title compound (2.1 g) as a pale-brown solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-03f1bb9463d64664841c15e5acdee4b6
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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