Methanol → 2-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylthiophenyl) thiazole

HRID 1378597Notes

Reaction equation

HRID 1378597 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)Br.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[S:24].CO>C(O)C>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]1[S:24][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 27348242-ChlorothiobenzamideHCID 537994631-(2-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromo ethanone

Product 1

HCID 539795112-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylthiophenyl) thiazoleYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone from Step 3 (1.39 g, 4.1 mmol) and 2-chlorothiobenzamide (0.71 g, 4.1 mmol) in 10 mL of ethanol was heated to reflux for 4.4 hours. The solution was cooled to room temperature and poured into 25 mL of methanol, chilled with an ice bath whereupon crystals of pure product formed which were isolated by filtration and air dried to afford the thiazole (1.34 g, 79%): mp 117°-119° C. 1H NMR (CDCl3) 300 MHz 8.37 (m, 1H), 7.62 (m, 2H), 7.49 (d, J=7.7Hz,1H), 7.32 (m, 7H), 7.22 (d, J=8.5Hz, 2H), 2.51 (s, 3H). Mass spectrum M+ +H=412.

Workup

  1. temperatureto reflux for 4.4 hours
  2. temperaturechilled with an ice bath whereupon crystals of pure product
  3. customformed which
  4. customwere isolated by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-b701e2d725d546379db794ba1ebfcbe9
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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