Water → HCID 68778575, compound

HRID 2263198Notes

Reaction equation

HRID 2263198 reaction equation
Br[C:2]1[S:3][C:4]([CH2:13][CH3:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:13]([C:4]1[S:3][C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)=[N:6][C:5]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 68778379HCID 68778379, compound

Product 1

HCID 68778575HCID 68778575, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-5-ethyl-4-phenyl-1,3-thiazole (4.00 g, 14.9 mmol), tert-butyl piperazine-1-carboxylate (8.33 g, 44.7 mmol) and potassium carbonate (2.06 g, 14.9 mmol) in dimethylformamide (50 ml) was stirred at 120° C. for 13 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the desired product (2.35 g, 42.2%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-e47f9f336b8c432ca359f7280bfbfba8
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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