4-Isothiocyanato-2-(trifluoromethyl)benzonitrile → HCID 86668137, compound

HRID 2370357Notes

Reaction equation

HRID 2370357 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15]C)=O)[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:10].[F:19][C:20]([F:33])([F:32])[C:21]1[CH:28]=[C:27]([N:29]=[C:30]=[S:31])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N:11]2[C:12]([CH3:18])([CH3:17])[C:13](=[O:15])[N:29]([C:27]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:20]([F:33])([F:19])[F:32])[CH:28]=3)[C:30]2=[S:31])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:10]

Participants

5

Reactant 2

HCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 66732501HCID 66732501, compound

Product 1

HCID 86668137HCID 86668137, compoundYield 4.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound was prepared according to General Method 1. A solution of methyl 2-(3-fluoro-4-(methoxymethyl)phenylamino)-2-methylpropanoate (60 mg, 0.24 mmol) and 2-(trifluoromethyl)-4-isothiocyanatobenzonitrile (120 mg, 0.52 mmol) in DMSO (1 mL) was heated at 82° C. for 12 h. The reaction mixture was poured in water (10 mL) and extracted with ethyl acetate. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by silica gel chromatography (100-200 mesh) to obtain 5 mg of final product, HPLC, Column: YMC ODS AQ, 4.6×250 mm, 5 μm, Mobile Phase A: 0.05% TFA, Mobile Phase B: ACN, Gradient: 10% to 90% B in 10 min, hold for 10 min. 90% to 10% B in 1 min, Flow Rate: 1 mL/min, Retention time: 13.316 min, M+1, 452.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel chromatography (100-200 mesh)

Sources & evidence

ORD record
ord-133a70dcff744c0f8d7d8167f798ea25
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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