2-(4-methoxyphenoxy)ethanethioamide → HCID 54443028, compound

HRID 1378603Notes

Reaction equation

HRID 1378603 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][O:21][C:22]1[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([NH2:30])=[S:29])=[CH:24][CH:23]=1>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:30]=[C:28]([CH2:27][O:26][C:25]3[CH:31]=[CH:32][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[S:29][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27435552-(4-methoxyphenoxy)ethanethioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

Product 1

HCID 54443028HCID 54443028, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone, (Example 1, Step 3) (2.30 g, 6.8 mmol) and 4-methoxyphenoxy thioacetamide (1.35 g, 6.8 mmol) in 20 mL of acetonitrile was heated to reflux for 1.1 hours. The solution was concentrated in vacuo and the residue dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford a solid that was recrystallized from a mixture of ethyl acetate and isooctane to provide pure 4- (4-fluorophenyl) -5- (4-methylthiophenyl)-2-((4-methoxyphenoxy) methyl) thiazole (1.60 g; 54%): mp 89°-92° C., 1H NMR (CDCl3) 300 MHz 7.47 (dd, J=3.2, 8.7Hz, 2H), 7.23 (d, J=8.5 Hz, 2H), 7.17 (d, J=8.5Hz, 2H), 6.98 (m, 4H), 6.86 (d, J=9.1 Hz, 2H), 5.33 (s, 2H), 3.78 (s, 3H), 2.49 (s,3H). 19F NMR (CDCl3) -114.07 (m). Mass spectrum M+H+=438.

Workup

  1. temperatureto reflux for 1.1 hours
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with saturated aqueous NaHCO3, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a solid
  9. customthat was recrystallized from a mixture of ethyl acetate and isooctane

Sources & evidence

ORD record
ord-4f7b63049ad1495db58f39e962909493
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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