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

HRID 65029Notes

Reaction equation

HRID 65029 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>[NH2:1][C:2]1[S:3][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:4]=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

In 40 ml of acetonitrile was dissolved 516 mg of thiourea. In the solution was suspended 2.5 g of 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)-ethanone hydrobromide. To the suspension was added dropwise slowly 0.95 ml of triethylamine while stirring. The mixture was stirred for 3 hours at a refluxing temperature, which was then left standing for cooling. Precipitating crystals were collected by filtration. The crystals were washed with an aqueous solution of saturated hydrogen carbonate, water, ethanol and ethylether in that order, followed by drying. The crystals were recrystallised from tetrahydrofuran to yield 1.5 g (90%) of 2-amino-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazol, m.p. 265°-266° C.

Workup

  1. stirringThe mixture was stirred for 3 hours at a refluxing temperature, which
  2. waitwas then left standing
  3. temperaturefor cooling
  4. customPrecipitating crystals
  5. filtrationwere collected by filtration
  6. washThe crystals were washed with an aqueous solution of saturated hydrogen carbonate, water, ethanol and ethylether in that order
  7. customby drying
  8. customThe crystals were recrystallised from tetrahydrofuran

Sources & evidence

ORD record
ord-474e362800e249e193c25c2149262056
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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