Hydrochloric Acid → HCID 15951526, compound

HRID 245013Notes

Reaction equation

HRID 245013 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][O:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:29]#N)([CH3:28])[CH3:27])=[CH:21][CH:20]=1.C[OH:33].Cl>CN(C=O)C.O>[CH3:16][O:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:26]([CH3:27])([CH3:28])[C:29](=[O:33])[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:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 13639520Methyl 4-[(2-cyanopropan-2-yl)amino]benzoate

Product 1

HCID 15951526HCID 15951526, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-isothiocyanato-2-trifluoromethylbenzonitrile (1a) (0.228 g, 1 mmol) and 4-[(cyanodimethylmethyl)-amino]-benzoic acid methyl ester (49b) (0.14 g, 0.64 mmol) in DMF (2 ml) was heated under microwave irradiation at 60° C. for 12 hours. To this mixture were added methanol (6 ml) and aq. 2N HCl (2 ml). The second mixture was refluxed for 4 h. After being cooled to room temperature, the reaction mixture was poured into cold water (10 ml) and extracted with ethyl acetate (3×30 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane; dichloromethane:acetone, 75:25) to yield 4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]benzoic acid methyl ester (49c) [RD152] (0.18 g, 0.4 mmol, 63%), the structure of which is illustrated in Formula 19, as a white powder.

Workup

  1. temperatureThe second mixture was refluxed for 4 h
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (dichloromethane; dichloromethane:acetone, 75:25)

Sources & evidence

ORD record
ord-0b2be370639243678381bdb40f34cf9c
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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