Sodium Hydroxide → HCID 178507365, compound

HRID 1711426Notes

Reaction equation

HRID 1711426 reaction equation
[C:1]1([S:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=3)[NH:14][N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:29].[Sn].[OH-:36].[Na+]>C(Cl)(Cl)Cl.CCOC(C)=O.CO.Cl.C(Cl)Cl>[C:1]1([S:11]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=3)[NH:14][N:13]=2)(=[O:29])=[O:36])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 5352426Tin atomHCID 59304173HCID 59304173, compound

Product 1

HCID 178507365HCID 178507365, compound

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(1-naphthylsulfanyl)-5-nitro-1H-indazole (5.50 g, 17.11 mmol) and 3-chloroperoxybenzoic acid (17.91 g, 103.80 mmol) in CHCl3 was stirred at room temperature for 4 hours, diluted with EtOAc, washed sequentially with Na2SO3 solution, water and brine, dried over Na2SO4, and concentrated in vacuo to give a residue. A mixture of this residue, tin mossy (15.79 g, 133.01 mmol) in MeOH and conc. hydrochloric acid was heated at 60° C., cooled to room temperature, diluted with CH2Cl2 and basified with NaOH. The phases were separated. The aqueous phase was extracted with CH2Cl2. The organic phase and the extracts were combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue was purified chromatographically, to provide the title compound, 2.50 g, (45% overall yield), characterized by HNMR and mass spectral analyses. MS (ES+) m/e 324 (MH+).

Workup

  1. washwashed sequentially with Na2SO3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. temperaturewas heated at 60° C.
  6. temperaturecooled to room temperature
  7. customThe phases were separated
  8. extractionThe aqueous phase was extracted with CH2Cl2
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe resultant residue was purified chromatographically
  12. customto provide

Sources & evidence

ORD record
ord-a520f823e7db4c13800e025ac85a8258
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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