Dicyclohexylcarbodiimide → Methyl 4-(2,3,4-trimethoxyphenylacetyl)-1-piperazinecarbodithioate

HRID 1460190

Reaktionsgleichung

Reaktionsgleichung von HRID 1460190
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]([OH:16])=O.[N:17]1([C:23]([S:25][CH3:26])=[S:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]([N:20]1[CH2:21][CH2:22][N:17]([C:23]([S:25][CH3:26])=[S:24])[CH2:18][CH2:19]1)=[O:16]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 897272,3,4-Trimethoxyphenylacetic acidHCID 21278808Methyl piperazine-1-carbodithioate

Produkt 1

HCID 19388512Methyl 4-(2,3,4-trimethoxyphenylacetyl)-1-piperazinecarbodithioateAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 6.2 ml of methylene chloride were dissolved 310 mg (1.37 mmol.) of 2,3,4-trimethoxyphenylacetic acid and 289 mg (1.64 mmol.) of methyl 1-piperazinecarbodithioate. To the solution was added 395 mg (1.92 mmol.) of dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 1 hour. A precipitated solid was removed by filtration, and to the filtrate were added methylene chloride and 1-N hydrochloric acid. The organic solvent portion was taken out, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill off the solvent. The residue was purified over a silica gel column. The obtained oil was crystallized from a mixture of ethanol and hexane, yielding 257 mg of the desired compound as a white crystalline product, m.p. 119°-120° C., yield 48.8%.

Aufarbeitung

  1. customA precipitated solid was removed by filtration
  2. additionto the filtrate were added methylene chloride and 1-N hydrochloric acid
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationto distill off the solvent
  6. customThe residue was purified over a silica gel column
  7. customThe obtained oil was crystallized from a mixture of ethanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-a46d335b64cc465aa82a48abd19e2846
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070089

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