Water → HCID 68777852, compound

HRID 2263022Notes

Reaction equation

HRID 2263022 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[N:3]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.O>CN(C)C=O>[S:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:4]1[N:3]=[C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)[S:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27358235-Chloro-3-(2-thienyl)-1,2,4-thiadiazole

Product 1

HCID 68777852HCID 68777852, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-3-(2-thienyl)-1,2,4-thiadiazole (4.80 g, 23.7 mmol) and tert-butyl piperazine-1-carboxylate (4.41 g, 23.7 mmol) in dimethylformamide (50 ml) was added triethylamine (13.2 ml, 94.7 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was poured to the reaction mixture, and the resulting solution 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 recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 4.33 g (51.9%) of the desired product as a solid.

Workup

  1. extractionthe resulting solution 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 recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-09651ac4969b493181448efc97fae428
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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