2,2-Dimethylpropanethioamide → 2-(Tert-butyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

HRID 1378576Notes

Reaction equation

HRID 1378576 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]([CH3:26])([CH3:25])[C:22]([NH2:24])=[S:23]>C(O)C.C(OCC)(=O)C>[C:21]([C:22]1[S:23][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:24]=1)([CH3:26])([CH3:25])[CH3:20]

Participants

5

Reactant 2

HCID 30311302,2-DimethylpropanethioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

Product 1

HCID 542839112-(Tert-butyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazoleYield 78.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone (Example 1, Step 3) (0.196 g, 0.578 mmol) in ethanol (6 mL) in a 25 mL round bottom flask was added 2,2-dimethylthiopropionamide from Step 1 (0.071 g, 0.606 mmol) and the mixture heated to reflux overnight. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and this solution washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and concentrated in vacuo yielding 2-(tert-butyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as a pale yellow oil (0.162 g, 78%): 1H NMR (CDCl3) 300 mHz δ7.56-7.51 (m, 2H), 7.24 (d, J=8.48 Hz, 2H), 7.20 (d, J=8.48 Hz, 2H), 6.98 (t, J=8.85 Hz, 2H), 2.49 (s, 3H), 1.52 (s, 9H). MS (EI): m/e 357 (M+). HRMS Δ=0.1 mmu.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux overnight
  3. washthis solution washed successively with Na2CO3 (10% solution) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96a33e1f5bfe42e3bde27b9d76417c7c
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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