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

HRID 1378592
Notes
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Reaction equation

HRID 1378592 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 27435542-(3,5-Dichlorophenoxy)ethanethioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

Product 1

HCID 539346704-(4-Fluorophenyl)-5-(4-methylthiophenyl)-2-((3,5-dichlorophenoxy)methyl)thiazoleYield 74%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887Methanol
Solvent
HCID 6342AcetonitrileSolvent

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

  1. temperatureto reflux for 1.2 hours
  2. customa precipitate formed
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes