Sodium Chloride → HCID 24855847, compound

HRID 418002Notes

Reaction equation

HRID 418002 reaction equation
[N:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([N:15](CC)CC)C.[C:20]([N:27]1C=CN=C1)(N1C=CN=C1)=[S:21].O.NN.[Cl-].[Na+]>O1CCCC1>[NH:27]([C:20]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH2:3]1)=[S:21])[NH2:15]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 802641,1'-ThiocarbonyldiimidazoleHCID 207112Ethyl piperazine-1-acetate

Product 1

HCID 24855847HCID 24855847, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl piperazine-1-acetate (680 mg, 3.71 mmol) in tetrahydrofuran (8.0 mL) was mixed with triethylamine (0.776 mL, 5.57 mmol) and thiocarbonyldiimidazole (992 mg, 5.57 mmol) at room temperature and stirred at room temperate for 2 hours and then stirred with hydrazine monohydrate (0.272 mL, 5.57 mmol) for another 2 hours. The reaction solution was mixed with saturated aqueous sodium chloride and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated to give the crude preparation of the desired product (115% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customto give the crude

Sources & evidence

ORD record
ord-ba694221e7224f2c802e7ae1c1416377
Source dataset
uspto-grants-2012_01
Patent number
US08093251B2

Reaction notes

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