Triethylamine → HCID 9935075, compound

HRID 1418038Notes

Reaction equation

HRID 1418038 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=O.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH:24]([N:28]([CH2:32][CH2:33][CH3:34])[C:29]([NH2:31])=[S:30])[CH2:25][O:26][CH3:27].C(N(CC)CC)C>C(O)C>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:31]=[C:29]([N:28]([CH:24]([CH2:25][O:26][CH3:27])[C:15]2[CH:16]=[CH:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)[CH2:32][CH2:33][CH3:34])[S:30][C:2]=1[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-oneHCID 10979577HCID 10979577, compound

Product 1

HCID 9935075HCID 9935075, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

0.93 g of 2-bromo-1-(2,4-dichlorophenyl)propan-1-one, 1 g of N-(1-naphth-2-yl-2-methoxyethyl)-N-propyl-thiourea and 0.47 ml of triethylamine are dissolved in 20 ml of ethanol and the reaction mixture is heated for 3 hours at 70° C. The ethanol is removed by evaporation and then, successively, water is added, extraction is carried out with methylene chloride and the organic phases are washed, dried over sodium sulphate, filtered and concentrated under vacuum. The residue is purified on a column of silica gel, using a 9/1 (v/v) cyclohexane/ethyl acetate mixture as eluent, to provide 0.9 g of the expected product, the hydrochloride of which is prepared; M.p.=50° C. 1H NMR (DMSO): 0.73 (m, 3H), 1.12-1.59 (m, 2H), 2.09 (s, 3H), 3.35 (s, 3H), 3.31-3.46 (m, 2H), 3.97-4.23 (m, 2H), 5.48-5.60 (m, 1H), 7.48-7.95 (m, 10H).

Workup

  1. customThe ethanol is removed by evaporation
  2. additionsuccessively, water is added
  3. extractionextraction
  4. washthe organic phases are washed
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue is purified on a column of silica gel

Sources & evidence

ORD record
ord-2b34b3bf17334559988a871f18d618f6
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

Loading…