4-Isothiocyanato-2-(trifluoromethyl)benzonitrile → HCID 86668136, compound

HRID 2370347Notes

Reaction equation

HRID 2370347 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]([O-:16])=O)=[CH:8][CH:7]=1.[Na+].[F:21][C:22]([F:35])([F:34])[C:23]1[CH:30]=[C:29]([N:31]=[C:32]=[S:33])[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>>[CH3:19][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:13]([CH3:18])([CH3:17])[C:14](=[O:16])[N:31]([C:29]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:22]([F:35])([F:21])[F:34])[CH:30]=3)[C:32]2=[S:33])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 66732900HCID 66732900, compound

Product 1

HCID 86668136HCID 86668136, compoundYield 17%

Conditions

Temperature
100 °C

Procedure

Compound 8 was prepared according to General Method 3. A mixture of sodium 2-(4-(2-(dimethylamino)ethoxy)phenylamino)-2-methylpropanoate (107 mg, 0.37 mmol) and 2-(trifluoromethyl)-4-isothiocyanatobenzonitrile (107 mg, 0.44 mmol) was heated at 100° C. for 1 h then 82° C. for 12 h. The crude product was purified by silica gel chromatography using 100-200 Mesh silica gel (10% methanol in DCM) to obtain 30 mg of 4-(3-(4-(2-(dimethylamino)ethoxy)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile. The product was converted its HCl salt by treating with ethanolic HCl, HPLC, Column: HYPERSIL GOLD C18, 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: 9.568 min, M+1, 477.

Workup

  1. customCompound 8 was prepared
  2. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1fdac018bb77454eb264d19d0572cfaf
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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