2-methylthiazole-4-carbothioamide → HCID 22912398, compound

HRID 1378601Notes

Reaction equation

HRID 1378601 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)Br)=[CH:4][CH:3]=1.[CH3:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[S:28])[NH2:27])[N:25]=1>C(#N)C.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:27]=[C:26]([C:24]3[N:25]=[C:21]([CH3:20])[S:22][CH:23]=3)[S:28][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27443652-methylthiazole-4-carbothioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

Product 1

HCID 22912398HCID 22912398, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone (9.69 g, 28.6 mmol) (Example 1, Step 3) and 2-methylthiazole-4-thiocarboxamide (3.90 g, 24.7 mmol) in 35 mL of acetonitrile and 20 mL of ethanol was heated to reflux for 1 hour. The solution was concentrated in vacuo and the residue was dissolved in ethyl acetate, washed with saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a yellow solid. The crude solid was purified by flash chromatography over silica gel eluting with 1:1 hexane:ethyl acetate. The appropriate fractions were combined and the solvent removed in vacuo to provide pure 4-(4-fluorophenyl)-5-(4-methylthiophenyl)-2-[2-(methyl)-4-thiazolyl]thiazole (4.79 g; 49%): mp 132.5°-135° C. 1H NMR (CDCl3) 300 MHz 7.89 (s, 1H), 7.55 (m, 2H), 7.25 (d, J=8.5Hz, 2H), 7.17 (d, J=8.5Hz, 2H), 7.01 (t, J=8.8Hz, 2H), 2.78 (s, 3H), 2.49 (s, 3H). 19F NMR (CDCl3) -113.80 (m). Mass spectrum M+H+ =399.

Workup

  1. temperatureto reflux for 1 hour
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaHCO3, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow solid
  9. customThe crude solid was purified by flash chromatography over silica gel eluting with 1:1 hexane
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-01fd508f80a244c2b7c190185e0fc4bd
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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