Thioanisole → 3-hydroxy-5-[(1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamide

HRID 1175850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175850
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([O:19]CC2C=CC=CC=2)[CH:18]=1)[C:8]([NH:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)=[O:9])[CH3:3].C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[OH:19][C:17]1[CH:16]=[C:7]([CH:6]=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:18]=1)[C:8]([NH:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)=[O:9]

Komponenten

4

Edukt 2

HCID 7520ThioanisoleHCID 53629624HCID 53629624, Verbindung

Produkt 1

HCID 230930393-hydroxy-5-[(1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamideAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel2×

Versuchsvorschrift

3-[(1-Methylethyl)oxy]-5-[(phenylmethyl)oxy]-N-1,3-thiazol-2-ylbenzamide (11.2 g) was dissolved in trifluoroacetic acid (60 mL) and treated with thioanisole (17.8 mL). The mixture was left to stir at ambient temperature for 18 hours before the trifluoroacetic acid was removed in vacuo. The residues were treated with isohexane (100 mL) and the solid filtered off, before being washed with further isohexane (2×20 mL). The solid was dissolved in ethyl acetate (200 mL) and washed with aqueous saturated sodium hydrogen carbonate solution (100 mL). The organics were washed with water (100 mL) and brine (100 mL), and dried (MgSO4) before evaporation in vacuo to afford a solid which was washed with isohexane (200 mL) and dried in vacuo to give the desired compound (7.18 g). 1H NMR δ (d6-DMSO): 1.27 (d, 6H), 4.55 (m, 1H), 6.49 (m, 1H), 7.02 (s, 1H), 7.14 (s, 1H), 7.25 (d, 1H), 7.54 (d, 1H), 9.73 (s, 1H), 12.44 (s, 1H). m/z 279 (M+H)+, 277 (M−H)−

Aufarbeitung

  1. waitThe mixture was left
  2. customwas removed in vacuo
  3. additionThe residues were treated with isohexane (100 mL)
  4. filtrationthe solid filtered off
  5. washbefore being washed with further isohexane (2×20 mL)
  6. dissolutionThe solid was dissolved in ethyl acetate (200 mL)
  7. washwashed with aqueous saturated sodium hydrogen carbonate solution (100 mL)
  8. washThe organics were washed with water (100 mL) and brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. custombefore evaporation in vacuo
  11. customto afford a solid which
  12. washwas washed with isohexane (200 mL)
  13. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-32b7a796598d4b79904568ec87861282
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842694B2

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