Hydrochloric Acid → (4RS)-4-(3-bromophenyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride

HRID 2229839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229839
C([NH:5][C:6]([NH:8][CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:19]>>[ClH:19].[Br:18][C:14]1[CH:13]=[C:12]([CH:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)[CH:17]=[CH:16][CH:15]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 11232800N-(tert-butyl)-N'-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea

Produkt 1

HCID 18469310(4RS)-4-(3-bromophenyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 0.5 g of N-(tert-butyl)-N′-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea in 3.8 cm3 of 6N hydrochloric acid is heated with stirring at a temperature in the region of 100° C. for 5 hours 30 minutes. The reaction medium is then cooled to a temperature in the region of 20° C. A white precipitate forms, which is filtered off after stirring for 30 minutes. The filter cake is rinsed with diethyl ether and then dried in an oven under reduced pressure (10 Pa) at a temperature in the region of 60° C., after which it is purified by chromatography, under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-63μ; diameter 1.5 cm; height 20 cm), eluting with a dichloromethane/methanol mixture (90/10 by volume). The fractions containing the expected product are collected. These fractions are combined and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.1 g of (4RS)-4-(3-bromophenyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride is obtained in the form of a white solid. (Rf=0.26 in a 90/10 by volume dichloromethane/methanol mixture, on a Merck 60F254R silica plate). [1H NMR spectrum (250 MHz, d6-(CD3)SO, δ in ppm): 3.45 (dd, J=14 and 8 Hz: 1H); 3.97 (dd, J=14 and 8.5 Hz : 1H); 5.42 (dd, J=8.5 and 8 Hz: 1H); from 7.35 to 7.55 (mt: 2H); from 7.55 to 7.75 (mt: 2H); from 9.10 to 10.90 (broad unres. mult.: 1H)].

Aufarbeitung

  1. temperatureis heated
  2. temperatureThe reaction medium is then cooled to a temperature in the region of 20° C
  3. filtrationA white precipitate forms, which is filtered off
  4. stirringafter stirring for 30 minutes
  5. washThe filter cake is rinsed with diethyl ether
  6. customdried in an oven under reduced pressure (10 Pa) at a temperature in the region of 60° C.
  7. customafter which it is purified by chromatography, under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 40-63μ; diameter 1.5 cm; height 20 cm), eluting with a dichloromethane/methanol mixture (90/10 by volume)
  9. additionThe fractions containing the expected product
  10. customare collected
  11. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-8e25f79cdaa646d4a18a794cf2f7f3a8
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420566B2

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