2-(3-Chlorophenoxy)ethanethioamide → 2-((3-Chlorophenoxy)methyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

HRID 1378599Notes

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:22]=[C:23]([CH:29]=[CH:30][CH:31]=1)[O:24][CH2:25][C:26]([NH2:28])=[S:27]>C(#N)C.C(O)C.CO>[Cl:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][CH:31]=1)[O:24][CH2:25][C:26]1[S:27][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:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone (1.98 g, 5.84 mmol) (Example 1, Step 3) and 3-chlorophenoxy thioacetamide (1.18 g, 5.85 mmol) in 15 mL of acetonitrile and 10 mL of ethanol was heated to reflux for 16 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 solid was air dried and then recrystallized from methanol to provide (1.67 g; 65%),of pure 2-((3-chlorophenoxy)methyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole: mp 106°-110° C., 1NMR (CDCl3) 300 MHz 7.50 (m, 2H), 7.30-7.15 (m, 5H), 7.09-6.87 (m, 5H), 5.38 (s, 2H), 2.50 (s, 3H). 19F NMR (CDCl3) -113.58 (m). Mass spectrum M+ =441.

Workup

temperatureto reflux for 16 hours
customa precipitate formed
customthat was removed by filtration
customdried
customrecrystallized from methanol

Sources & evidence

ORD record: ord-c539cfa3b49e46d6b3c6595a5ce75224
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668161

Reaction notes

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