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

HRID 1062616Notes

Reaction equation

HRID 1062616 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 (0.52 g) in acetonitrile (40 mL) was added 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide (2.5 g) and triethylamine (0.95 mL) was slowly added dropwise with stirring. After completion of dropwise addition, the mixture was stirred at a refluxing temperature for 3 h, and after allowing to cool, the precipitated crystals were collected by filtration. The crystals were washed successively with saturated sodium hydrogencarbonate solution, water, ethanol and ethyl ether and dried. The obtained crude crystals were recrystallized from tetrahydrofuran to give the title compound (1.5 g, yield 90%).

Workup

  1. additionwas slowly added dropwise
  2. additionAfter completion of dropwise addition
  3. stirringthe mixture was stirred at a refluxing temperature for 3 h
  4. temperatureto cool
  5. filtrationthe precipitated crystals were collected by filtration
  6. washThe crystals were washed successively with saturated sodium hydrogencarbonate solution, water, ethanol and ethyl ether
  7. customdried
  8. customThe obtained crude crystals
  9. customwere recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-e133ce62de6947f8bb67d304a85fa7b6
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

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