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

HRID 65028Notes

Reaction equation

HRID 65028 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].Br.Br[CH:8]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O.C(N(CC)CC)C>C(#N)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:5]=[C:3]([NH:2][CH3:1])[S:4][C:8]=2[C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723704MethylthioureaHCID 114633362-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 30248932-Thiazolamine, 4-(4-methoxyphenyl)-N-methyl-5-(3-pyridinyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 18 ml of acetonitrile was dissolved 242 mg of N-methylthiourea. In the solution was suspended 1.0 g of 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide. To the suspension was added dropwise slowly 0.4 ml of triethylamine while stirring. The mixture was stirred for three hours at refluxing temperature, and 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 recrystallized from ethyl acetate isopropyl ether to yield 650 mg (85%) of 4-(4-methoxyphenyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole, m.p. 158°-159° C.

Workup

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

Sources & evidence

ORD record
ord-bb24533325394783b807fb1be28f16d2
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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