N-(Phenylmethyl)thiourea → HCID 10274859, compound

HRID 1378588Notes

Reaction equation

HRID 1378588 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:29][C:30]([NH2:32])=[S:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:32]=[C:30]([NH:29][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:31][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 737375N-(Phenylmethyl)thioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 10274859HCID 10274859, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.415 g, 1.12 mmol) in isopropanol (12 mL) in a 25 mL round bottom flask was added N-benzyl thiourea (0.186 g, 1.12 mmol). The solution was heated to reflux (30 hours), cooled to room temperature and let stand for 7 days. The resulting suspension was concentrated in vacuo. The resulting residue was suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate, filtered and reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-benzylaminothiazole as a pale yellow solid (0.34 g, 69%): mp 112° C. 1H NMR (CDCl3 400 mHz δ7.74 (d, J=8.56 Hz, 2H), 7.43-7.25 (m, 10H), 6.92 (t, J=8.56 Hz, 2H), 4.33 (s, 2H), 3.02 (s, 3H). MS (EI-thermospray): m/z 439 (MH+). HRMS Δ=1.6 mmu.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux (30 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

Sources & evidence

ORD record
ord-51622289c9d741eb9323d66ddfb5d9f3
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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