Diethyl Ether → 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

HRID 83858Notes

Reaction equation

HRID 83858 reaction equation
[Cl: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].C(OCC)C>CC(O)=O>[Cl: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]([SH:13])=[N:11][CH:10]=2)([CH3:24])[CH3:23])=[CH:4][C:3]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 866622441-(3-(4-Chloro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)thiourea

Product 1

HCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiolYield 94,698.797%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(3-(4-chloro-3-methoxyphenyl)-3-methyl-2-oxobutyl)-3-(4-fluorophenyl)-thiourea (21) (230 g, 0.58 mmol) in HOAc (1 L) was heated to reflux for 4 h with mechanical stirring. The reaction mixture was cooled and evaporated to give a residue which was treated with diethyl ether to give 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (22) (207 g, 95%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.91-7.19 (d, 1H), 6.86-6.88 (t, 2H), 6.81 (s, 1H), 6.86-6.91 (t, 2H), 6.81 (s, 1H), 6.59-6.63 (m, 2H), 6.50-6.53 (d, 2H), 6.45 (s, 1H), 3.74 (s, 3H), 1.46 (s, 6H).

Workup

  1. temperatureto reflux for 4 h with mechanical stirring
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. customto give a residue which

Sources & evidence

ORD record
ord-1d98af56f45a4a4b839df78af7a6d383
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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