Triethylamine → 2-Ethyl-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole

HRID 65030Notes

Reaction equation

HRID 65030 reaction equation
[C:1]([NH2:5])(=[S:4])[CH2:2][CH3:3].Br[CH:7]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O.C(N(CC)CC)C>C(#N)C>[CH2:2]([C:1]1[S:4][C:7]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2760628PropanethioamideHCID 114633372-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone

Product 1

HCID 135188862-Ethyl-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazoleYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 40 ml of acetonitrile was dissolved 493 mg of thiopropionic acid amide. In the solution was suspended 2.15 g of 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone. To the suspension was added dropwise slowly 0.78 ml of triethylamine while stirring. The mixture was stirred for 3 hours at a refluxing temperature, then the solvent was evaporated off. To the residue was added a saturated aqueous solution of sodium hydrogen carbonate. The mixture was subjected to extraction with ethyl acetate. The extract was dried, then the solvent was evaporated off. The residue was recrystallised from ethyl acetate-isopropyl ether to yield 1.38 g (91%) of 2-ethyl-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole, m.p. 59°-60° C.

Workup

  1. stirringThe mixture was stirred for 3 hours at a refluxing temperature
  2. customthe solvent was evaporated off
  3. additionTo the residue was added a saturated aqueous solution of sodium hydrogen carbonate
  4. extractionThe mixture was subjected to extraction with ethyl acetate
  5. customThe extract was dried
  6. customthe solvent was evaporated off
  7. customThe residue was recrystallised from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-9d3e44a81a0c491c88d9be5f26fc44e9
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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