2-(3,5-Dichlorophenoxy)ethanethioamide → 4-(4-Fluorophenyl)-5-(4-methylthiophenyl)-2-((3,5-dichlorophenoxy)methyl)thiazole

HRID 1378592Notes

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]=[C:30]([Cl:32])[CH:31]=1)[O:24][CH2:25][C:26]([NH2:28])=[S:27]>C(#N)C.C(O)C.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:28]=[C:26]([CH2:25][O:24][C:23]3[CH:29]=[C:30]([Cl:32])[CH:31]=[C:21]([Cl:20])[CH:22]=3)[S:27][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

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone, (Example 1, Step 3) (4.01 g, 11.8 mmol) and 3,5-dichlorophenoxy thioacetamide (2.80 g, 11.9 mmol) in 20 mL of acetonitrile and 10 mL of ethanol was heated to reflux for 1.2 hours. The solution was diluted with methanol, cooled to 0° C. in an ice bath and a precipitate formed that was removed by filtration to provide pure 4-(4-fluorophenyl)-5-(4-methylthiophenyl)-2-((3,5-dichlorophenoxy)methyl)thiazole (4.19 g; 74%) which was used directly in the next step: mp 104.5°-105.0° C.; Mass spectrum M+H=476.

Workup

temperatureto reflux for 1.2 hours
customa precipitate formed
customthat was removed by filtration

Sources & evidence

ORD record: ord-641a16a0ef314a878d1734ecb3ced5a1
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668161

Reaction notes

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