4-Methoxybenzenecarbothioamide → HCID 66864148, compound

HRID 1186702Notes

Reaction equation

HRID 1186702 reaction equation
Br[CH:2]([C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=O)[C:3]([O:5][CH3:6])=[O:4].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](=[S:24])[NH2:23])=[CH:20][CH:19]=1>CC#N>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[N:23]=[C:22]([C:21]3[CH:25]=[CH:26][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[S:24][C:2]=2[C:3]([O:5][CH3:6])=[O:4])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7368274-MethoxybenzenecarbothioamideHCID 24745534Methyl 2-bromo-3-(4-fluorophenyl)-3-oxopropanoate

Product 1

HCID 66864148HCID 66864148, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of methyl 2-bromo-3-(4-fluorophenyl)-3-oxopropanoate 78 (1 equiv, 1.15 g, 4.2 mmol) in MeCN at room temperature was added 4-methoxybenzo-thioamide 77 (1 equiv, 700 mg, 4.2 mmol) and the reaction mixture was stirred for 18 h. The solvent was evaporated and the residue purified by trituration with diethyl ether to afford methyl 4-(4-fluorophenyl)-2-(4-methoxyphenyl)thiazole-5-carboxylate 79 (320 mg, 22% yield). LRMS (ESI): (calc) 343.37 (found) 344.235 (MH+)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-6992462e472b4f3a8a90d69298f2c7d2
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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