2-Bromo-1-(2-chloro-4-methoxyphenyl)-propan-1-one → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-(N-naphth-1-yl-N-propylamino)thiazole

HRID 1418036

Reaktionsgleichung

Reaktionsgleichung von HRID 1418036
[C:1]1([N:11]([CH2:15][CH2:16][CH3:17])[C:12]([NH2:14])=[S:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH:19]([CH3:31])[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[Cl:30])=O>CO>[Cl:30][C:23]1[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=1[C:20]1[N:14]=[C:12]([N:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH2:15][CH2:16][CH3:17])[S:13][C:19]=1[CH3:31]

Komponenten

4

Edukt 2

HCID 110549852-Bromo-1-(2-chloro-4-methoxyphenyl)-propan-1-oneHCID 54008331N-Naphth-1-yl-N-propylthiourea

Produkt 1

HCID 675729324-(2-Chloro-4-methoxyphenyl)-5-methyl-2-(N-naphth-1-yl-N-propylamino)thiazoleAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution containing 0.5 g of N-naphth-1-yl-N-propylthiourea and 0.5 g of 2-bromo-1-(2-chloro-4-methoxyphenyl)propan-1-one in 15 ml of methanol is heated at reflux for 6 hours. The reaction mixture is then evaporated to dryness and then, successively, the residue is taken up in water, basified with 33% sodium hydroxide and extracted with ethyl acetate and the organic phase is dried over sodium sulphate, filtered and concentrated under vacuum. The residue is then purified on a column of silica gel eluted with ethyl acetate, to provide 0.56 g of a yellow oil. 1H NMR (CDCl3): 0.97 (t, J=7.7, 3H, --CH2 --CH3), 1.73 (sex, 2H, --CH2 --CH3), 2.04 (s, 3H, --CH3), 3.82 (s, 3H, --OCH3), 3.90 (m, 2H, --CH2 --CH2 --CH3), 6.89 (dd, J=1.8, J=8.0, 1H, H5arom) 7.02 (d, J=1.8, 1H, H3arom), 7.50-7.70 (m, 4H, H2, H3, H8 and H6arom), 7.85-8.10 (m, H, H6, H7, H4 and H5).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. customThe reaction mixture is then evaporated to dryness
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue is then purified on a column of silica gel
  9. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bfca4796c9024b8a85a51878e027c27f
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05880135

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