Water → 2-(2-Chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole

HRID 1378573Notes

Reaction equation

HRID 1378573 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.C(#N)C.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH2:28])=[S:27].O>C(OCC)(=O)C>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]1[S:27][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)[N:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 27348242-ChlorothiobenzamideHCID 53723114HCID 53723114, compound

Product 1

HCID 537138882-(2-Chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazoleYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 100 mL one-neck round-bottom flask equipped for magnetic stirring was charged with 2-bromo-2-(4-methylthiophenyl)-1(4-methylphenyl)ethanone from Step 3 (0.300 g, 0.895 mmol) and acetonitrile (20 mL). 2-Chlorothiobenzamide (0.154 g, 0.895 mmol) was added, and the suspension was heated and held at reflux for three hours. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and poured into water(50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic solution was dried over MgSO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (silica gel; 5% ethyl acetate in hexane) to yield 2-(2-chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole (0.284 g, 78%) as a white solid: mp 125°-126° C. 1H NMR (CDCl3) 300 MHz 8.40(m, 1H), 7.62-7.11(m, 11H), 2.50 (s, 3H), 3.36(s, 3H). Mass spectrum: MH+ =407.

Workup

  1. customA 100 mL one-neck round-bottom flask equipped
  2. temperaturethe suspension was heated
  3. temperatureat reflux for three hours
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  6. dry with materialThe combined organic solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified via flash chromatography (silica gel; 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5f687ffb93de4f259cda757ddc72fbb4
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

Loading…