Dicyclohexylcarbodiimide → Dicyclohexylthiourea

HRID 1287266

Reaktionsgleichung

Reaktionsgleichung von HRID 1287266
C1(NC(=[S:10])NC)CCCC1.[CH:11]1([N:17]=[C:18]=[N:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>O1CCOCC1>[CH:20]1([NH:19][C:18]([NH:17][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[S:10])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 14229902N'-cyclopentyl-methyl-thiourea

Produkt 1

HCID 727200Dicyclohexylthiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2.44 g of N-[4 -(β-<2-methoxy-5-methyl-benzamido>-ethyl)-benzenesulfonyl]-N'-cyclopentyl-methyl-thio-urea (I) were dissolved together with 1.03 g of dicyclohexylcarbodiimide in 20 ml of hot dioxane. The whole was allowed to cool and to stand for several days. Thereupon, the N,N'-dicyclohexyl-thiourea that had formed (melting point 176° - 178° C) was filtered off with suction. The filtrate which contained the N-[4-(β-<2-methoxy-5-methyl-benzamido>ethyl)-benzenesulfonyl]-N'-cyclopentyl-methyl-carbodiimide (II) in dissolved state, was combined with about 5 ml of water. The whole was shortly heated on a water bath and concentrated. The residue was dissolved in a mixture of toluene, ether and dilute aqueous ammonia, while shaking. The aqueous phase was separated. The toluene/ether phase was extracted again with dilute ammonia. The aqueous extracts were united and acidified. There was obtained a precipitate, constituting the N-[4-(β-<2-methoxy-5-methyl-benzamido>-ethyl)-benzenesulfonyl]-N'-cyclopentylmethylurea (III). After recrystallization from methanol, the sulfonylurea was found to melt at 148° - 150° C.

Aufarbeitung

  1. temperatureto cool
  2. waitto stand for several days

Quellen und Nachweise

ORD-Eintrag
ord-d012b2481da043038729ca452b6d89d2
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03984416

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