Diethyl Ether → 1-t-Butyl-1-(3-toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide

HRID 21674

Reaktionsgleichung

Reaktionsgleichung von HRID 21674
[C:1]([N:5]([C:7]([C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1)=[O:8])[NH2:6])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])=[CH:19][CH:18]=1.CCOCC>C(Cl)Cl>[C:1]([N:5]([C:7]([C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1)=[O:8])[NH:6][C:27]([NH:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)(=[O:24])=[O:25])=[O:28])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 1385874-Chlorobenzenesulfonyl isocyanateHCID 15452040N'-t-butyl-N'-(3-methylbenzoyl)hydrazine

Produkt 1

HCID 193678331-t-Butyl-1-(3-toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N'-t-butyl-N'-3-toluoyl hydrazine (4.03 g, 0.02 mol) in methylene chloride (25 ml) under nitrogen was added 4-chlorobenzenesulfonyl isocyanate (5 g, 80%, 0.02 mol) at room temperature. The exothermic reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure to give an oil. A precipitate appeared after treating with ether. The pure product was collected by suction-filtration and washed with a small amount of ether affording 4.8 g of 1-t-butyl-1-(3-toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide as a white solid: m.p. 184°-188° C.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customto give an oil
  3. filtrationThe pure product was collected by suction-filtration
  4. washwashed with a small amount of ether affording 4.8 g of 1-t-butyl-1-(3-toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-45bd01d7a9434ff7980c9999d945be63
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424333

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