Thiourea, butyl- → HCID 22912058, compound

HRID 1378610Notes

Reaction equation

HRID 1378610 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:26][C:27]([NH2:29])=[S:28])[CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:22]([NH:26][C:27]1[S:28][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:29]=1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 1551919Thiourea, butyl-HCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 22912058HCID 22912058, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2- (4-methylsulfonylphenyl) ethanone (Example 26, Step 2) (0.384 g, 1.03 mmol) in ethanol (15 mL) in a 25 mL round bottom flask was added N-butylthiourea (0.144 g, 1.09 mmol). The solution was heated to reflux for 14 hours and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate, filtered and concentrated yielding 2-butylamino-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole (0.319 g, 77%) as an off-white fluffy solid: mp 134°-135° C., 1HNMR (DMSO d6) 7.94 (t, J=5.37 Hz, 1 H), 7.78 (d, J=8.79, 2 H), 7.45-7.36 (m, 4 H), 7.15 (t, J=8.79 Hz, 2H), 3.25 (q, J=5.37 Hz, 2 H), 3.18 (s, 3 H), 1.58-1.50 (m, 2 H), 1.41-1.32 (m, 2H), 0.90 (t, J=7.33 Hz, 3 H); MS (EI) m/z 404 (M+). HRMS Δ=1.1 mmu.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 14 hours
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. washwashed with NaHCO3 saturated solution (3×10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ce46e2b514441b795834737f83ebe8d
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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