Triethylamine → N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea

HRID 1280601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280601
Cl.[NH2:2][C@H:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:4][OH:5].[C:16]([N:20]=[C:21]=[S:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[C:16]([NH:20][C:21]([NH:2][C@H:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:4][OH:5])=[S:22])([CH3:19])([CH3:18])[CH3:17]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11544tert-Butyl isothiocyanate2×HCID 69885645(2R)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride

Produkt 1

HCID 86584418N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 0.92 g of (2R)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride and 0.6 cm3 of tert-butyl isothiocyanate in 10 cm3 of ethanol is cooled to a temperature in the region of 0° C. and 0.56 cm3 of triethylamine is then added. The mixture is stirred for 18 hours at room temperature and is then heated at a temperature in the region of 60° C. for 2 hours; the suspension thus dissolves. 0.6 cm3 of tert-butyl isothiocyanate is added and heating is continued for 3 hours, after which the reaction medium is concentrated under reduced pressure (2 kPa) at a temperature in the region of 50° C. The yellow oil obtained is dissolved in 50 cm3 of ethyl acetate, after which the organic solution is washed with twice 50 cm3 of sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.2 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-nitrobenzyl)-ethyl]thiourea are obtained in the form of a yellow oil. 1H NMR spectrum (300 MHz, (CD3)2SO-d6 with addition of a few drops of CD3COOD-d4, δ in ppm): 1.39 (s: 9H); 2.98 (limiting AB: 2H); 3.38 (limiting AB: 2H); 4.48 (mt: 1H); 7.60 (t, J=8 Hz: 1H); 7.74 (broad d, J=8 Hz: 1H); 8.09 (broad d, J=8 Hz: 1H); 8.16 (broad s: 1H).

Aufarbeitung

  1. additionis then added
  2. temperatureis then heated at a temperature in the region of 60° C. for 2 hours
  3. dissolutionthe suspension thus dissolves
  4. temperatureheating
  5. waitis continued for 3 hours
  6. concentrationafter which the reaction medium is concentrated under reduced pressure (2 kPa) at a temperature in the region of 50° C
  7. customThe yellow oil obtained
  8. washafter which the organic solution is washed with twice 50 cm3 of sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-06bc91a545cf4ed3bb7f1d2040d76f2e
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451821B1

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