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

反応式

HRID 1418036 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 675729324-(2-Chloro-4-methoxyphenyl)-5-methyl-2-(N-naphth-1-yl-N-propylamino)thiazole収率 73.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bfca4796c9024b8a85a51878e027c27f
出典データセット
uspto-grants-1999_03
特許番号
US05880135

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