N-Iodosuccinimide → HCID 18699441, compound

HRID 1421280Notes

Reaction equation

HRID 1421280 reaction equation
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:14]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=2[Cl:23])[N:13]=[C:12]([C:24]#[N:25])[CH:11]=1>C(#N)C.ClCCl>[NH2:9][C:10]1[N:14]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=2[Cl:23])[N:13]=[C:12]([C:24]#[N:25])[C:11]=1[I:1]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 22618590HCID 22618590, compound

Product 1

HCID 18699441HCID 18699441, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

N-Iodosuccinimide (17.67 g) was added portionwise to a stirred solution of 5-amino-3-cyano-1-(2,4,6-trichlorophenyl)pyrazole (U.S. Pat. No. 5,232,940; 22.5 g) in acetonitrile (300 ml) and the resulting mixture stirred at room temperature for 1 hour, then evaporated under reduced pressure. The residue was partially purified by chromatography on silica gel (800 g), using an elution gradient of dichloromethane:ethyl acetate (100:0 to 0:100), to produce a pale brown solid which was further purified as follows. Trituration with hexane (25 ml) provided a residue which was dissolved in dichloromethane (500 ml). This solution was washed with water (500 ml), the aqueous washing back-washed with ethyl acetate (500 ml) and the combined organic solutions dried (Na2SO4) and evaporated under reduced pressure to furnish the title compound as a pale brown solid. δ(DMSOd6): 6.28 (br.s,2H), 7.98 (s,2H). MS (thermospray): M/Z [M+H] 413.0; C10H4Cl3 lN4 +H requires 412.9.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was partially purified by chromatography on silica gel (800 g)
  3. customto produce a pale brown solid which
  4. customwas further purified
  5. customTrituration with hexane (25 ml) provided a residue which
  6. washThis solution was washed with water (500 ml)
  7. washthe aqueous washing
  8. washback-washed with ethyl acetate (500 ml)
  9. dry with materialthe combined organic solutions dried (Na2SO4)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-edf6437a0e264745985d2703b8d94bc1
Source dataset
uspto-grants-2000_06
Patent number
US06075043

Reaction notes

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