Propyl-2-thiourea → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole

HRID 1378590Notes

Reaction equation

HRID 1378590 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH2:22]([NH:25][C:26]([NH2:28])=[S:27])[CH2:23][CH3:24]>C(O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:28]=[C:26]([NH:25][CH2:22][CH2:23][CH3:24])[S:27][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1615208Propyl-2-thioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 102220054-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazoleYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (0.346 g, 0.932 mmol) (Example 26, Step 2) in ethanol (15 mL) in a 25 mL round bottom flask was added N-propylthiourea (0.116 g, 0.979 mmol) with stirring. The resulting solution was heated to reflux for 24 hours. The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in methylene chloride, washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole as a yellow crystalline solid (0.276 g, 76%): mp 181°-182° C. 1H NMR (DMSO-d6) 400 mHz 5 7.97 (t, J=5.37 Hz, 1H), 7.78 (d, J=8.79 Hz, H), 7.42 (dd, J=5.86, 8.79, 2H), 7.37 (d, J=8.79, H), 7.15 (t, J=8.79 Hz, 2H), 3.21 (q, J=6.84, H), 3.18 (s, 3H), 1.60 (m, 2H), 0.91 (t, J=7.33, H). MS (EI): m/z 390 (M+). HRMS Δ=2.4 mmu.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed successively with Na2CO3 (10% solution) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ce25a412db7344eb9878091fd1dd5aa6
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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