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 1418036Notes

Reaction equation

HRID 1418036 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bfca4796c9024b8a85a51878e027c27f
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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