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

HRID 1280611

Reaktionsgleichung

Reaktionsgleichung von HRID 1280611
C([NH:5][C:6]([NH:8][C@H:9]([CH2:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[CH2:10]O)=[S:7])(C)(C)C.C(O)C.C(OCC)C.[ClH:26]>CC(C)=O>[ClH:26].[S:15]1[CH:16]=[CH:17][C:13]([CH2:12][C@@H:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)=[CH:14]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 86584422N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-thienylmethyl)ethyl]thiourea

Produkt 1

HCID 69884756(-)-(4R)-4-(3-thienylmethyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 0.94 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-thienylmethyl)ethyl]thiourea in 9.2 cm3 of 6N hydrochloric acid is heated at a temperature in the region of 100° C. with stirring for 3 hours and is then concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. A greenish oil is obtained, which is taken up in 10 cm3 of acetone to give a sticky gum. 1.5 cm3 of ethanol are then added, followed by dropwise addition, with stirring, of 6 cm3 of diethyl ether. The crystals obtained are filtered off on a sinter funnel, washed with diethyl ether and then dried in an oven under vacuum (10 Pa) at a temperature in the region of 50° C. 0.5 g of (−)-(4R)-4-(3-thienylmethyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride is obtained in the form of gray crystals melting at 152° C. 1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 2.99 (mt: 2H); 3.26 (dd, J=11 and 5.5 Hz: 1H); 3.59 (dd, J=11 and 8 Hz: 1H); 4.54 (mt: 1H); 7.10 (dd, J=5.5 and 1 Hz 1H); 7.38 (mt: 1H); 7.54 (dd, J=5 and 3 Hz: 1H); from 9.15 to 10.55 (broad unres. mult.: 3H). (αD20=−4.3±0.5 at a concentration of 0.5% in methanol).

Aufarbeitung

  1. concentrationis then concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C
  2. customA greenish oil is obtained
  3. customto give a sticky gum
  4. additionfollowed by dropwise addition
  5. customThe crystals obtained
  6. filtrationare filtered off on a sinter funnel
  7. washwashed with diethyl ether
  8. customdried in an oven under vacuum (10 Pa) at a temperature in the region of 50° C

Quellen und Nachweise

ORD-Eintrag
ord-4aa95af5f0c84f41a9c234890001b1c0
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451821B1

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