2-(2-Chlorophenoxy)ethanethioamide → HCID 54014773, compound

HRID 1378600Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone (2.05 g, 6.04 mmol) (Example 1, Step 3) and 2-chlorophenoxy thioacetamide (1.21 g, 6.0 mmol) in 30 mL of acetonitrile was heated to reflux for 3 hours. The solution was diluted with methanol, cooled to 0° C. in an ice bath and a precipitate formed that was removed by filtration. The crude solid was further purified by flash chromatography over silica gel and the appropriate fractions were combined, concentrated in vacuo and crystallized from methanol to provide 2.60 g (98%) of pure 4-2- ((2 -chlorophenoxy) methyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl) thiazole: mp 126°-129° C., 1H NMR (CDCl3) 300 MHz 7.55-7.39 (m, 4H), 7.28-6.90 (m, 8H), 5.44 (s, 2H), 2.49 (s, 3H). 19F NMR (CDCl3) -114.00 (m). Mass spectrum M+H+ =442.

Workup

temperatureto reflux for 3 hours
customa precipitate formed
customthat was removed by filtration
customThe crude solid was further purified by flash chromatography over silica gel
concentrationconcentrated in vacuo
customcrystallized from methanol

Sources & evidence

ORD record: ord-f90fb59fd7e84caca5fb0bea9679fe43
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668161

Reaction notes

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