Trifluoroacetic acid → 2-(4,4-Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-fluorobenzonitrile

HRID 1093038Notes

Reaction equation

HRID 1093038 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:10]2[CH2:14][C:13]([CH3:16])([CH3:15])[N:12](CC3C=CC(OC)=CC=3)[S:11]2(=[O:27])=[O:26])[CH:3]=1.FC(F)(F)C(O)=O>ClCCl.CO>[CH3:15][C:13]1([CH3:16])[NH:12][S:11](=[O:27])(=[O:26])[N:10]([C:4]2[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=2[C:6]#[N:7])[CH2:14]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579051604-Fluoro-2-(5-(4-methoxybenzyl)-4,4-dimethyl-1,1'-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile

Product 1

HCID 579049732-(4,4-Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-fluorobenzonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-2-(5-(4-methoxybenzyl)-4,4-dimethyl-1,1′-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile (4.6 g, 11.81 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (2.73 mL, 35.4 mmol) and the mixture stirred at room temperature for 18 h. The mixture was diluted with methanol and the white solid collected by filtration and discarded. The cloudy solution was concentrated and the resulting solid was triturated with methanol and then filtered to give the title compound as a white solid (3.18 g, 100% yield). LCMS (M+H) calcd for C11H13FN3O2S: 270.07; found: 270.00. 1H NMR (300 MHz, CDCl3) δ: 7.66 (0.2H, dd, J=8.8, 5.8 Hz), 7.58 (1H, dd, J=9.5, 2.6 Hz), 7.10-7.04 (1H, m), 4.48 (1H, brs), 3.85 (2H, s), 1.55 (6H, s).

Workup

  1. filtrationthe white solid collected by filtration
  2. concentrationThe cloudy solution was concentrated
  3. customthe resulting solid was triturated with methanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0a88495e7be64b26a1e9c634181295db
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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