Trifluoroacetic acid → 2-cyclopentyl-6-methoxybenzo[d]isothiazol-3(2H)-one

HRID 404963Notes

Reaction equation

HRID 404963 reaction equation
FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=O.[CH:22]1([NH:27][C:28](=[O:38])[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=2[SH:37])[CH2:26][CH2:25][CH2:24][CH2:23]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:22]1([N:27]2[C:28](=[O:38])[C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=3[S:37]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12041285BistrifluoroacetoxyiodobenzeneHCID 50994688N-cyclopentyl-2-mercapto-4-methoxybenzamide

Product 1

HCID 250674602-cyclopentyl-6-methoxybenzo[d]isothiazol-3(2H)-oneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bis(trifluoroacetoxy)iodobenzene (PIFA) (0.645 g, 1.5 mmol) in CH2Cl2 was added to a solution of N-cyclopentyl-2-mercapto-4-methoxybenzamide (0.251 g, 1 mmol) and trifluoroacetic acid (TFA) (0.23 mL, 3 mmol) in CH2Cl2 at 0° C. The resulting mixture was gradually warmed to room temperature. After 1 h, the solvent was evaporated under reduced pressure and the resulting residue was purified by column chromatography using dichloromethane to afford 2-cyclopentyl-6-methoxybenzo[d]isothiazol-3(2H)-one as a white solid (84%, 0.210 g). 1H NMR (300 MHz, CDCl3): δ 7.87 (d, 1H, J=8.5 Hz), 6.93 (s, 1H), 6.92 (d, 1H, J=8.2 Hz), 5.50-5.01 (m, 1H), 3.86 (s, 3H), 2.13-2.12 (m, 2H), 1.83-1.67 (m, 6H). LC-MS (ESI) Calcd for C13H15NO2S [M+H]+: 250.08. Found: 249.95.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-d314b775ae4e4470a1cacbe65ffa6e93
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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