Hydrogen Peroxide → HCID 11619554, compound

HRID 2242764Notes

Reaction equation

HRID 2242764 reaction equation
[OH:1]O.[NH2:3][C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[C:7]([C:21]#[N:22])=[C:6]([C:23]#[N:24])[C:5]=1[S:25][C:26]([F:29])([F:28])[F:27].C(Cl)Cl.O>FC(F)(F)C(O)=O>[NH2:3][C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:17])([F:18])[F:19])=[CH:11][C:10]=2[Cl:20])[C:7]([C:21]#[N:22])=[C:6]([C:23]#[N:24])[C:5]=1[S:25]([C:26]([F:29])([F:28])[F:27])=[O:1]

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 6344DichloromethaneHCID 11583112HCID 11583112, compound

Product 1

HCID 11619554HCID 11619554, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

Hydrogen peroxide (278 mg, 35%, 2.9 mmol) was added to solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-2,3-dicyano-4-trifluoromethylthiopyrrole (850 mg, 1.9 mmol) in trifluoroacetic acid (10 ml). The resulting solution was stirred at 20° C. for 0.75 hour. Another portion of hydrogen peroxide ( 0.97 mmol) was added and the mixture stirred at 20° C. for a further hour. The reaction mixture was poured into methylene chloride (60 ml) and water (60 ml) and the organic layer washed with water (2×), dried (sodium sulfate), concentrated and purified by chromatography on silica gel, eluting with heptane/ethyl acetate (4:1) to give the title compound as a yellow solid (293 mg, 0.64 mmol); 19F-NMR: −64.35, −75.59.

Workup

  1. stirringthe mixture stirred at 20° C. for a further hour
  2. washthe organic layer washed with water (2×)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel
  6. washeluting with heptane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-5ead847c14274dbb8394e6285608cab3
Source dataset
uspto-grants-2010_03
Patent number
US07674474B2

Reaction notes

Loading…