2,2,4-Trimethylpentane → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole

HRID 1378615Notes

Reaction equation

HRID 1378615 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.[Cl:22][C:23]1[CH:24]=[C:25]([NH:30][C:31]([NH2:33])=[S:32])[CH:26]=[C:27]([Cl:29])[CH:28]=1.C(CC(C)(C)C)(C)C>C(O)C.C(OCC)(=O)C.C(Cl)Cl>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:33]=[C:31]([NH:30][C:25]3[CH:24]=[C:23]([Cl:22])[CH:28]=[C:27]([Cl:29])[CH:26]=3)[S:32][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

6

Reactant 3

HCID 109072,2,4-TrimethylpentaneHCID 27375393,5-DichlorophenylthioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 229121444-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazoleYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.312, 0.841 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-(3,5-dichlorophenyl)thiourea (0.195 g, 0.882 mmol). The solution was heated to reflux (14 hours) and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in ethyl acetate (100 mL) and washed with sodium carbonate solution (10%, 3×20 mL), brine (1×20 mL), dried over sodium sulfate, filtered and concentrated, yielding a powdery solid. This solid was dissolved in ethyl acetate/methylene chloride. Addition of isooctane resulted in the precipitation of 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole (0.261 g, 63%) as a pale yellow powder: mp 287°-288° C.; 1HNMR (DMSO d6) 400 mHz 10.84 (s, 1 H), 7.86 (d, J=8.79 Hz, 2 H), 7.73 (s, 2 H), 7.54-7.45 (m, 4 H), 7.22 (t, J=8.79 Hz, 2 H), 7.15 (s, 1 H), 3.22 (s, 3 H); MS m/z 492 (M+). HRMS Δ=4.8 mmu.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux (14 hours)
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. washwashed with sodium carbonate solution (10%, 3×20 mL), brine (1×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customyielding a powdery solid

Sources & evidence

ORD record
ord-8d8550e06b2948dca937c246d6f1e992
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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