Acetic Acid → N-(2-aminophenyl)-5-phenyl-4-isothiazolin-3-one

HRID 35898Notes

Reaction equation

HRID 35898 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:11]1)([O-])=O.C(O)(=O)C.C(O)C>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:11]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 15294642N-(2-nitrophenyl)-5-phenyl-4-isothiazolin-3-one

Product 1

HCID 15294636N-(2-aminophenyl)-5-phenyl-4-isothiazolin-3-oneYield 49.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.560 g (1.880 mmol) N-(2-nitrophenyl)-5-phenyl-4-isothiazolin-3-one, 0.450 g (excess) iron powder, 1 mL glacial acetic acid and 15 mL absolute ethanol was stirred at reflux for one hour. The mixture was allowed to cool to room temperature, poured into 150 mL water and extracted with three 100 mL portions of ethyl acetate. The organic layers were combined, dried, filtered and solvent was evaporated. The resulting solid was recrystallized from ethanol/water to provide 0.250 g (0.930 mmol, 49%) N-(2-aminophenyl) -5-phenyl-4-isothiazolin-3-one, mp=145°-146° C.- NMR (CDCl13 /TMS): 4.15 (bs, 2H), 6.6 (s, 1H), 6.8-7.6 (m, 9H). IR (Nujol): 3358, 3216, 1658. High resolution mass spectrum: Calculated; 269. 074860. Measured; 269.074265. Anal. calcd. for C15H12N2OS: C 67.14, H 4.51, N 10.44, S 11.95; Found C 66.76, H 4.43, N 10.19, S 12.09.

Workup

  1. temperatureat reflux for one hour
  2. extractionextracted with three 100 mL portions of ethyl acetate
  3. customdried
  4. filtrationfiltered
  5. customsolvent was evaporated
  6. customThe resulting solid was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-3f34df75e523449da5c5da6edd7d003a
Source dataset
uspto-grants-1995_05
Patent number
US05411977

Reaction notes

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