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

HRID 65036Notes

Reaction equation

HRID 65036 reaction equation
C[NH:2][C:3](=[S:14])[CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br.Br[CH:17]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=O.[CH2:34](N(CC)CC)C>C(#N)C>[CH3:34][N:5]([CH2:4][C:3]1[S:14][C:17]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:2]=1)[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114633362-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromideHCID 86740999HCID 86740999, compound

Product 1

HCID 542703132-(N-methylbenzoylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazoleYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 50 ml of acetonitrile was dissolved 2.3 g of N-methylbenzoylaminothioacetamide. In the solution was suspended 4.0 g of 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide. To the suspension was added while stirring 1.5 ml of triethylamine, followed by further stirring under reflux. The reaction solution was left standing for cooling, 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 solution was washed with water, dried, then, the solvent was evaporated off. The residue was purified by means of a silica-gel column chromatography (eluent: ethyl acetate) to give 3.2 g (yield 72%) of 2-(N-methylbenzoylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole.

Workup

  1. additionTo the suspension was added
  2. temperatureunder reflux
  3. waitThe reaction solution was left
  4. temperaturefor cooling
  5. customthe solvent was evaporated off
  6. additionTo the residue was added a saturated aqueous solution of sodium hydrogen carbonate
  7. extractionThe mixture was subjected to extraction with ethyl acetate
  8. washThe extract solution was washed with water
  9. customdried
  10. customthe solvent was evaporated off
  11. customThe residue was purified by means of a silica-gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-9f848ecc64be48a18d96b12f198eb7fd
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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