Hydrochloric Acid → HCID 15952779, compound

HRID 2273885Notes

Reaction equation

HRID 2273885 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)=[C:2]=[S:3].[CH3:16][C:17]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])[C:18]#N.C[OH:29].Cl>CN(C=O)C.O>[C:22]1([N:21]2[C:17]([CH3:16])([CH3:20])[C:18](=[O:29])[N:1]([C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:13])([F:15])[F:14])[CH:5]=3)[C:2]2=[S:3])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 751282-Anilino-2-methylpropiononitrileHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrile

Product 1

HCID 15952779HCID 15952779, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1a (0.274 g, 1.2 mmol) and 6a (0.160 g, 1 mmol) in dry DMF (0.2 ml) was stirred for 48 h. To this mixture were added methanol (10 ml) and 2N HCl (3 ml). The second mixture was refluxed for 6 h. After being cooled to room temperature, the reaction mixture was poured into cold water (20 ml) and extracted with ethyl acetate (20 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane) to yield 4-[3-phenyl-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 6b, [RD10] (0.276 g, 0.71 mmol, 71%) as a white powder.

Workup

  1. temperatureThe second mixture was refluxed for 6 h
  2. extractionextracted with ethyl acetate (20 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed (dichloromethane)

Sources & evidence

ORD record
ord-7b40673d05c5445b9cbbcd4c3a7c85de
Source dataset
uspto-grants-2015_09
Patent number
US09126941B2

Reaction notes

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