Methanol → 4-(3-(4-hydroxyphenyl)-4,4-diMethyl-5-oxo-2-thioxoiMidazolidin-1-yl)-2-(trifluoroMethyl)benzonitrile

HRID 1927316Notes

Reaction equation

HRID 1927316 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:14])([CH3:13])[C:11](=N)[N:10]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=3)[C:9]2=[S:28])=[CH:4][CH:3]=1.C[OH:30].O>Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])([CH3:14])[C:11](=[O:30])[N:10]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:17]=3)[C:9]2=[S:28])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 866098534-[3-(4-Hydroxyphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 159526854-(3-(4-hydroxyphenyl)-4,4-diMethyl-5-oxo-2-thioxoiMidazolidin-1-yl)-2-(trifluoroMethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3b (0.202 g, 0.5 mmol) in HCl aq., 2N (2 ml) and methanol (5 ml) was heated to reflux for 2 h. After being cooled to room temperature, the reaction mixture was poured into cold water (10 ml) and extracted with ethyl acetate (10 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane/acetone, 9:1) to yield 4-[3-(4-hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 3c, [RD8] (0.198 g, 0.49 mmol, 98%) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. extractionextracted with ethyl acetate (10 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (dichloromethane/acetone, 9:1)

Sources & evidence

ORD record
ord-f6e6d92b193944248e7b73bffffb98ea
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

Loading…