Dimethyl acetylenedicarboxylate → Methyl [3-cyclohexyl-2-(cyclohexylimino)-4-oxo-5-thiazolidinylidene]acetate

HRID 867451

Reaktionsgleichung

Reaktionsgleichung von HRID 867451
[CH:1]1([NH:7][C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[S:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][O:18][C:19]([C:21]#[C:22][C:23](OC)=[O:24])=[O:20]>CO>[CH3:17][O:18][C:19](=[O:20])[CH:21]=[C:22]1[S:9][C:8](=[N:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:23]1=[O:24]

Komponenten

4

Edukt 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 727200Dicyclohexylthiourea

Produkt 1

HCID 3967510Methyl [3-cyclohexyl-2-(cyclohexylimino)-4-oxo-5-thiazolidinylidene]acetateAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of N,N'-dicyclohexylthiourea (10.0 g, 42 mmoles) and dimethylacetylenedicarboxylate (7.8 g, 55 mmoles) in methanol (100 mls) is stirred at room temperature for 16 hours, then warmed on a steambath for 45 minutes and cooled. The precipitate is filtered off, rinsed with cold methanol and dried. This gave the product as white crystals, (11.3 g), mp 97°-98° C.

Aufarbeitung

  1. temperaturewarmed on a steambath for 45 minutes
  2. temperaturecooled
  3. filtrationThe precipitate is filtered off
  4. washrinsed with cold methanol
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-509049bbe55149f198cffb6800332198
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775677

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