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

HRID 2273878Notes

Reaction equation

HRID 2273878 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-a0db42bb05b048e3a799a3503a357ff5
Source dataset
uspto-grants-2015_09
Patent number
US09126941B2

Reaction notes

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