Hydrochloric Acid → 2-Aminomethyl-4-(1,1-dimethylethyl)-6-(methylthio)phenol hydrochloride

HRID 236920

Reaktionsgleichung

Reaktionsgleichung von HRID 236920
O[CH2:2][NH:3]C(=O)C[Cl:6].[CH3:8][S:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[OH:20].S(=O)(=O)(O)O.Cl>C(O)(=O)C.C(O)C>[ClH:6].[NH2:3][CH2:2][C:12]1[CH:13]=[C:14]([C:16]([CH3:17])([CH3:19])[CH3:18])[CH:15]=[C:10]([S:9][CH3:8])[C:11]=1[OH:20]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 62466N-Methylol-alpha-chloroacetamideHCID 123826074-Tert-butyl-2-(methylsulfanyl)phenol

Produkt 1

HCID 213146452-Aminomethyl-4-(1,1-dimethylethyl)-6-(methylthio)phenol hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Pulverized N-hydroxymethyl-2-chloroacetamide (3.32 g., 0.027 mole) is added portionwise over 15 minutes to a solution of 2-methylthio-4-(1,1-dimethylethyl)phenol (5.3 g., 0.027 mole) and conc. sulfuric acid (10 ml.) in acetic acid (150 ml.) cooled in an ice bath. The resulting reaction mixture is stirred at 20° C. for 16 hours and then poured into ice-water (1 l.) whereupon a white gum is deposited. The gum is extracted with ether and the etheral extract, washed well with water and saturated brine. Removal of the solvent under reduced pressure leaves a residual solid which is dissolved in ethanol (30 ml.). The resulting solution is treated with 12 N hydrochloric acid (15 ml.) and heated at reflux for 4 hours. Evaporation in vacuo affords a residual solid which is triturated with ether and collected by filtration to give crude 2-aminomethyl-4-(1,1-dimethylethyl)-6-(methylthio)phenol hydrochloride (5.4 g., 76.4%), m.p. 150°-177° C. Two recrystallizations from ether-ethanol (10:1; v:v) followed by recrystallization from 12 N hydrochloric acid provides analytically pure 2-aminomethyl-4-(1,1-dimethylethyl)6-(methylthio)phenol hydrochloride as colorless crystals, m.p. 180°-181.5° C.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customThe resulting reaction mixture
  3. extractionThe gum is extracted with ether
  4. washthe etheral extract, washed well with water and saturated brine
  5. customRemoval of the solvent under reduced pressure
  6. customleaves a residual solid which
  7. temperatureheated
  8. temperatureat reflux for 4 hours
  9. customEvaporation in vacuo
  10. customaffords a residual solid which
  11. customis triturated with ether
  12. filtrationcollected by filtration
  13. customto give crude 2-aminomethyl-4-(1,1-dimethylethyl)-6-(methylthio)phenol hydrochloride (5.4 g., 76.4%), m.p. 150°-177° C
  14. customTwo recrystallizations from ether-ethanol (10:1; v:v)
  15. customfollowed by recrystallization from 12 N hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-f9544dfcb4c94a96abfd576f2689e35d
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04159279

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