HCID 53752706, compound → HCID 67572974, compound

HRID 1418037Notes

Reaction equation

HRID 1418037 reaction equation
[CH2:1]([N:4]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2)[C:5]([NH2:7])=[S:6])[CH2:2][CH3:3].Br[CH:19]([CH3:31])[C:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[O:29][CH3:30])=O>C(O)C>[ClH:28].[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[N:7]=[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:8]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][CH:12]=[N:13]4)[S:6][C:19]=2[CH3:31])=[C:23]([O:29][CH3:30])[CH:24]=1

Participants

4

Reactant 2

HCID 53752706HCID 53752706, compound2×HCID 54029696HCID 54029696, compound

Product 1

HCID 67572974HCID 67572974, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 0.4 g of N-propyl-N-quinol-5-ylthiourea (Compound 31) and 0.5 g of 2-bromo-1-(4-chloro-2-methoxyphenyl)propan-1-one in 15 ml of ethanol is heated at reflux for 6 hours. The reaction mixture is evaporated to dryness and then, successively, the residue is taken up in water, basified with 33% sodium hydroxide and extracted with ethyl acetate. The residue is purified on a column of silica gel eluted with a 1/1 (v/v) ethyl acetate/hexane mixture, to provide 0.46 g of a yellow oil. 1H NMR (CDCl3): 0.91 (t, J=7.3, 3H, --CH3), 1.61-1.78 (m, 2H, --CH2 --CH3), 2.02 (s, 3H, heterocycle --CH3), 3.83 (s, 3H, --OCH3), 3.97 (t, J=7.5, 2H, --CH2 --N<), 6.88 (dd, J=2.5, J=8.4, 1H, H5), 7.0 (d, J=2.5, 1H, H3), 7.36 (d, J=8.5, 1H, H6), 7.46 (dd, J=4.2, J=8.6, 1H, H3,), 7.63 (d, J=7.2, 1H, H4,), 7.80 (t, J=7.9, 1H, H7,), 8.17 (d, J=8.4, 1H, H6,), 8.33 (d, J=8.4, 1H, H8,), 8.96-8.99 (m, 1H, H2,).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. customThe reaction mixture is evaporated to dryness
  4. extractionextracted with ethyl acetate
  5. customThe residue is purified on a column of silica gel
  6. washeluted with a 1/1 (v/v) ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-20785ba850d94556bc1ad650bc850429
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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