Iodine → 4,5,N-triphenyl-4-isothiazolin-3-one

HRID 35904Notes

Reaction equation

HRID 35904 reaction equation
[C:1]1([C:7](=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[SH:18])[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([C:7]2[C:8](=[O:9])[N:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:18][C:17]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 867486572,3,N-triphenyl-3-mercaptopropenamide

Product 1

HCID 152946394,5,N-triphenyl-4-isothiazolin-3-oneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 150 mg (0.450 mmol) 2,3,N-triphenyl-3-mercaptopropenamide and 25 mL methylene chloride was stirred at room temperature. Added was 115 mg (1 equiv.) of iodine followed by 116 mg (1 equiv.) of triethylamine and the mixture stirred for one hour. Solvent was evaporated and 50 mL ethyl acetate added and the mixture poured into 50 mL water. The organic layer was separated and washed with three 50 mL portions of water. The organic layer was dried, filtered and solvent was evaporated from the filtrate. The resulting solid was recrystallized from ethanol/water to provide 108 mg (0.327 mmol, 73%) 4,5,N-triphenyl-4-isothiazolin-3-one as a tan solid, mp=175°-176° C. NMR (CDCl3 /TMS): 7.30-7.72 (m, 15H). IR (KBr): 1656. Mass spectrum (CI): M/z=330 (M+H)+. Anal. calcd. for C21H15NOS: C 76.57, H 4.59, N 4.25, S 9.73; Found: C 76.25, H 4.40, N 4.19, S 9.81.

Workup

  1. additionAdded
  2. stirringthe mixture stirred for one hour
  3. customSolvent was evaporated
  4. addition50 mL ethyl acetate added
  5. additionthe mixture poured into 50 mL water
  6. customThe organic layer was separated
  7. washwashed with three 50 mL portions of water
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. customsolvent was evaporated from the filtrate
  11. customThe resulting solid was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-c5a340b13279485b9334be581060dcc0
Source dataset
uspto-grants-1995_05
Patent number
US05411977

Reaction notes

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