2,2,4-Trimethylpentane → 2-Benzyl-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

HRID 1378577Notes

Reaction equation

HRID 1378577 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.[C:20]1([CH2:26][C:27]([NH2:29])=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(CC(C)(C)C)(C)C>C(O)C.C(OCC)(=O)C.C(Cl)Cl>[CH2:26]([C:27]1[S:28][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:29]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 109072,2,4-TrimethylpentaneHCID 7313682-PhenylethanethioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

Product 1

HCID 541930592-Benzyl-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-l-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (Example 1, Step 3) (0.250 g, 0.737 mmol) in ethanol (9 mL) in a 25 mL round bottom flask was added 2-phenylthioacetamide (0.111 g, 0.737 mmol) and the mixture heated to reflux overnight. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL), washed successively with Na2CO3 (10 % solution) and brine, dried over Na2SO4, filtered and concentrated in vacuo yielding an oil. This oil was dissolved in methylene chloride and isooctane yielding a suspension. The solid was removed by filtration and the filtrate reconcentrated in vacuo yielding 2-benzyl-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as a yellow oil which was suitable based upon 1H NMR to be used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux overnight
  3. washwashed successively with Na2CO3 (10 % solution) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customyielding an oil
  8. customThe solid was removed by filtration

Sources & evidence

ORD record
ord-5ee239faebe043aea816df43e9d45ff0
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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