Triethylamine → 2-Thiazolamine, 4-(4-methoxyphenyl)-5-(3-pyridinyl)-

HRID 2304599Notes

Reaction equation

HRID 2304599 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br.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>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[N:1]=[C:2]([NH2:4])[S:3][C:7]=2[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 114633362-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 30248942-Thiazolamine, 4-(4-methoxyphenyl)-5-(3-pyridinyl)-Yield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of thiourea (516 mg) in acetonitrile (40 mL), was added 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide (2.5 g), and then triethylamine (0.95 mL) was added slowly dropwise to the mixture with stirring. After addition, the mixture was stirred at reflux for 3 h. After cooling, the crude crystalline was collected by filtration. The crystalline was washed with an aqueous saturated solution of sodium hydrogen carbonate, water, ethanol, and ethyl ether, in that order, and dried. The obtained crude crystalline was recrystallized from tetrahydrofuran to give the title compound (1.5 g, yield 90%).

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 3 h
  4. temperatureAfter cooling
  5. filtrationthe crude crystalline was collected by filtration
  6. washThe crystalline was washed with an aqueous saturated solution of sodium hydrogen carbonate, water, ethanol, and ethyl ether, in that order
  7. customdried
  8. customThe obtained crude
  9. customcrystalline was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-c535df6ef80140ada17f9a41b9ee72b3
Source dataset
uspto-grants-2002_08
Patent number
US06436966B1

Reaction notes

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