1-(3-(4-Fluoro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)thiourea → HCID 66740600, compound

HRID 83865Notes

Reaction equation

HRID 83865 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:24])([CH3:23])[C:9](=O)[CH2:10][NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[S:13])=[CH:4][C:3]=1[O:25][CH3:26]>CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:12](=[S:13])[NH:11][CH:10]=2)([CH3:24])[CH3:23])=[CH:4][C:3]=1[O:25][CH3:26]

Participants

3

Reactant 1

HCID 866622481-(3-(4-Fluoro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)thiourea

Product 1

HCID 66740600HCID 66740600, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(3-(4-fluoro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)-thiourea (45 g, 0.119 mol) in AcOH (500 mL) was heated at reflux overnight. The cooled reaction mixture was concentrated and triturated with Et2O to give 5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione (40.5 g, 94%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.90 (t, 3H), 6.81 (s, 1H), 6.61 (m, 2H), 6.50 (m, 2H), 3.76 (s, 3H), 1.46 (s, 6H); MS (ESI) m/z 361 (MH+).

Workup

  1. temperatureat reflux overnight
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated
  4. customtriturated with Et2O

Sources & evidence

ORD record
ord-73b92933cb444cc282abe7d3ef154937
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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