Hydrochloric Acid → HCID 69884714, Verbindung

HRID 1280674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280674
C([NH:5][C:6]([NH:8][C@@H:9]([CH2:18]O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[S:7])(C)(C)C.[ClH:20]>>[ClH:20].[OH:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C@@H:9]2[CH2:18][S:7][C:6]([NH2:5])=[N:8]2)=[CH:12][CH:13]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 86584448N-(tert-butyl)-N'-[(1R)-1-hydroxymethyl-2-(4-hydroxyphenyl)ethyl]thiourea

Produkt 1

HCID 69884714HCID 69884714, Verbindung

Versuchsvorschrift

A solution of 0.2 g of N-(tert-butyl)-N′-[(1R)-1-hydroxymethyl-2-(4-hydroxyphenyl)ethyl]-thiourea in 2.6 cm3 of 6N hydrochloric acid is heated at a temperature in the region of 110° C. for 18 hours. The reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 55° C. and is then taken up successively in 10 cm3 of isopropyl ether, 10 cm3 of diethyl ether, 10 cm3 of pentane, 10 cm3 of petroleum ether and 10 cm3 of isopropyl ether, concentrating under the same conditions as above between each wash. The solid obtained is dried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C. to give 0.098 g of (+)-(4R)-4-(4-hydroxybenzyl)-4,5-dihydro-2-thiazolylamine hydrochloride in the form of an orange-coloured solid [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 2.78 (dd, J=13.5 and 7.5 Hz: 1H); 2.88 (dd, J=13.5 and 5.5 Hz: 1H); 3.26 (dd, J=11.5 and 6 Hz: 1H); 3.55 (dd, J=11.5 and 7.5 Hz: 1H); 4.45 (mt: 1H); 6.74 (d, J=8.5 Hz: 2H); 7.07 (d, J=8.5 Hz: 2H); 9.09 (unresolved complex: 1H); 9.41 (s: 1H); 9.56 (unresolved complex: 1H); 9.97 (broad s: 1H); (αD20=+9.5+/−0.5 at a concentration of 0.5% in methanol)].

Aufarbeitung

  1. concentrationThe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 55° C.
  2. concentration10 cm3 of diethyl ether, 10 cm3 of pentane, 10 cm3 of petroleum ether and 10 cm3 of isopropyl ether, concentrating under the same conditions as above between each wash
  3. customThe solid obtained
  4. customis dried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-d61cbd6290c64bf2a5838c9e1189b0ca
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451821B1

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