Water → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinone

HRID 486104

Reaktionsgleichung

Reaktionsgleichung von HRID 486104
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[NH:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[S:20].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH3:4][C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:24]2[NH:18][C:19](=[S:20])[NH:21][C:22]2=[O:23])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 517045Sodium AcetateHCID 12740302-Thiohydantoin

Produkt 1

HCID 541342535-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinoneAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (30.0 g, 128 mmols), 2-thiohydantoin (14.8 g, 128 mmols), and sodium acetate (36 g) in acetic acid (200 ml) is stirred under nitrogen and heated to reflux. After 24 hours the mixture is allowed to cool, and is stirred into water (2 L). After an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinone (24.6 g), mp 278°-279° C. (dec).

Aufarbeitung

  1. temperatureheated to reflux
  2. temperatureto cool
  3. filtrationAfter an hour the product is filtered off
  4. washwashed three times with water
  5. customdried
  6. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a59b2f68367049babe8d084d0602202c
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290800

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