Iodine → 5-(4-carboxyphenyl)-N-phenyl-4-isothiazolin-3-one

HRID 35902Notes

Reaction equation

HRID 35902 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([SH:21])=[CH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].C(Cl)Cl.II>C(N(CC)CC)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:21][N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:12](=[O:13])[CH:11]=2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 807IodineHCID 6344DichloromethaneHCID 867486563-(4-carboxyphenyl)-3-mercapto-N-phenylpropenamide

Product 1

HCID 152946385-(4-carboxyphenyl)-N-phenyl-4-isothiazolin-3-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 0.30 g (1.00 mmol)3-(4-carboxyphenyl)-3-mercapto-N-phenylpropenamide and 50 mL methylene chloride was stirred at room temperature. Added was 0.25 g (1.00 mmol) iodine followed by 0.2 mL (excess) triethylamine and the mixture stirred for one hour. Solvent was evaporated and 250 mL ethyl acetate added. The mixture was washed with three 100 mL portions of water. The organic layer was dried, filtered and solvent was evaporated from the filtrate. The resulting solid was triturated in absolute ethanol and filtered to dryness to provide 0.16 g (0.54 mmol, 54%)5-(4-carboxyphenyl)-N-phenyl-4-isothiazolin-3-one as a pale, yellow powder, mp=260-261° C. NMR (d6 -DMSO/TMS): 7.08 (s, 1H), 7.39-8.07 (m, 9H), 13.30 (bs, 1H). IR (KBr): 1678, 1652. Mass spectrum (CI): M/z=298.0 (M+H)+.

Workup

  1. additionAdded
  2. stirringthe mixture stirred for one hour
  3. customSolvent was evaporated
  4. addition250 mL ethyl acetate added
  5. washThe mixture was washed with three 100 mL portions of water
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customsolvent was evaporated from the filtrate
  9. customThe resulting solid was triturated in absolute ethanol
  10. filtrationfiltered to dryness

Sources & evidence

ORD record
ord-2e692f64015c498284bbff59f6a36ba1
Source dataset
uspto-grants-1995_05
Patent number
US05411977

Reaction notes

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