Dicyclohexylcarbodiimide → S-(4-Isothiocyanatophenyl) 4-butylsulphanylthiobenzoate

HRID 1901394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1901394
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([S:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH3:19].[N:30]([C:33]1[CH:38]=[CH:37][C:36]([SH:39])=[CH:35][CH:34]=1)=[C:31]=[S:32]>ClCCl>[CH2:16]([S:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([S:39][C:36]2[CH:37]=[CH:38][C:33]([N:30]=[C:31]=[S:32])=[CH:34][CH:35]=2)=[O:27])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH3:19]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 4217574-(Butylthio)benzoic acidHCID 233673904-Isothiocyanatobenzene-1-thiol

Produkt 1

HCID 86750022S-(4-Isothiocyanatophenyl) 4-butylsulphanylthiobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N,N'-dicyclohexylcarbodiimide (1.95 g, 0.009 mol), was added in one portion to a stirred solution of compound 2 (1.67 g, 0.008 mol), compound 3 (1.59 g, 0.009 mol) and 4-(N-pyrrolidino)pyridine (0.39 g, 0.003 mol) in dry dichloromethane (50 ml) at room temperature. The reaction mixture was stirred at room temperature overnight. The product was extracted into ether (200 ml) and was washed with aqueous potassium hydroxide solution (5%, 2×250 ml). The ether layer was evaporated in vacuo and the product was purified by column chromatography [silica gel/petroleum fraction (bp 40°-60° C.), dichloromethane, 1:1] and was recrystallised from cyclohexane to afford a white solid which was dried in vacuo.

Aufarbeitung

  1. extractionThe product was extracted into ether (200 ml)
  2. washwas washed with aqueous potassium hydroxide solution (5%, 2×250 ml)
  3. customThe ether layer was evaporated in vacuo
  4. customthe product was purified by column chromatography [silica gel/petroleum fraction (bp 40°-60° C.), dichloromethane, 1:1]
  5. customwas recrystallised from cyclohexane
  6. customto afford a white solid which
  7. customwas dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-765656fb180749249d5ded94745e1ac8
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05578242

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