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Sulfuric Acid → 5-(tert-Butylsulfanyl)-2-propoxybenzamide

HRID 441295
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 441295
[C:1](O)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[CH2:11]([O:14][C:15]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][C:16]=1[C:17]([NH2:19])=[O:18])[CH2:12][CH3:13]>O>[C:1]([S:24][C:21]1[CH:22]=[CH:23][C:15]([O:14][CH2:11][CH2:12][CH3:13])=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6386tert-Butanol2×HCID 214203982-Propoxy-5-sulfanylbenzamide

Produkt 1

HCID 214204225-(tert-Butylsulfanyl)-2-propoxybenzamideAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

t-Butanol (16 g.) was added to an aqueous sulphuric acid solution (200 ml.; containing 75% w/w sulphuric acid) cooled in ice-water. The mixture was stirred until all the t-butanol had dissolved, and then 2-propoxy-5-mercaptobenzamide (20 g.; prepared as described in Reference Example 2) was added in small portions with stirring during 15 minutes. After all the solid had dissolved the mixture was allowed to warm up to room temperature and kept at that temperature for 15 minutes. The solution was diluted with water (600 ml.), and the precipitated solid was filtered off and dissolved in chloroform (200 ml.). The chloroform solution was then washed with aqueous sodium hydroxide solution (2N; 40 ml.) and then with water (3 × 20 ml.), and dried over sodium sulphate. The solvent was removed in vacuo and the residue was recrystallised from aqueous ethanol, to give 5-t-butylthio-2-propoxybenzamide (15 g.), m.p. 135.5° - 137.5° C.

Aufarbeitung

  1. dissolutionhad dissolved
  2. dissolutionAfter all the solid had dissolved the mixture
  3. waitkept at that temperature for 15 minutes
  4. filtrationthe precipitated solid was filtered off
  5. dissolutiondissolved in chloroform (200 ml.)
  6. washThe chloroform solution was then washed with aqueous sodium hydroxide solution (2N; 40 ml.)
  7. dry with materialwith water (3 × 20 ml.), and dried over sodium sulphate
  8. customThe solvent was removed in vacuo
  9. customthe residue was recrystallised from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b0dc525da98d4cafadf621a118e11685
Quelldatensatz
uspto-grants-1977_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04039544

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