Triethylamine → 4-(5-Indanyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole

HRID 65033Notes

Reaction equation

HRID 65033 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].Br.Br[CH:8]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14]2)=O.C(N(CC)CC)C>C(#N)C>[CH2:16]1[C:17]2[C:13](=[CH:12][C:11]([C:9]3[N:5]=[C:3]([NH:2][CH3:1])[S:4][C:8]=3[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723704MethylthioureaHCID 137146742-Bromo-1-(5-indanyl)-2-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 137146904-(5-Indanyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 40 ml of acetonitrile was dissolved 661 mg. of N-methyl thiourea. In the solution was suspended 2.9 g of 2-bromo-1-(5-indanyl)-2-(3-pyridyl)ethanone hydrobromide. To the suspension was added dropwise slowly 1 ml of triethylamine. The mixture was then stirred for 2 hours at refluxing temperature, followed by being left standing for cooling. The solvent was then 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 and, then, the solvent was evaporated off. Recrystallization was conducted from ethyl acetate-isopropylether afforded 1.8 g (80%) of 4-(5-indanyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole, m.p. 169°-170° C.

Workup

  1. temperatureat refluxing temperature
  2. waitby being left
  3. temperaturefor cooling
  4. customThe solvent was then evaporated off
  5. additionTo the residue was added a saturated aqueous solution of sodium hydrogen carbonate
  6. extractionThe mixture was subjected to extraction with ethyl acetate
  7. washThe extract solution was washed with water
  8. customdried
  9. customthe solvent was evaporated off
  10. customRecrystallization

Sources & evidence

ORD record
ord-2f4230d73f514a46bb7feb07ed4a6ccb
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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