Trichloromethanethiol → Tert-butyl 4-(5-chloro-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylate

HRID 2263353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263353
[NH2:1][C:2](=[NH:16])[N:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cl:17][C:18]([SH:21])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:17][C:18]1[S:21][N:1]=[C:2]([N:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:8]2)[N:16]=1

Komponenten

6

Edukt 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 15197650Tert-butyl 4-carbamimidoylpiperazine-1-carboxylate

Produkt 1

HCID 66523695Tert-butyl 4-(5-chloro-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylateAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-[amino(imino)methyl]piperazine-1-carboxylate (1.50 g, 5.67 mmol) and perchloromethyl mercaptan (0.609 ml, 5.67 mmol) in dichloromethane (20 ml) was added dropwise a solution of sodium hydroxide (0.907 g, 22.7 mmol) in water (2.5 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 1.03 g (59.5%) of the desired product as a solid.

Aufarbeitung

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-457bab2709b24d4496d234e6ab42e904
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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