Sodium Carbonate → HCID 178478704, compound

HRID 2240093Notes

Reaction equation

HRID 2240093 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(S[C:35]2[C:43]3C(=CC=C([N+]([O-])=O)C=3)N[N:36]=2)C2C(=CC=CC=2)C=CC=1.[Cl:47]C1C=C(C=CC=1)C(OO)=O.[Sn].[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.CCOC(C)=O.CO.Cl.C(Cl)Cl>[ClH:47].[ClH:47].[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH:23][CH2:43][CH2:35][NH2:36])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

12

Reactant 6

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 5352426Tin atomHCID 59304173HCID 59304173, compoundHCID 178507365HCID 178507365, compound

Product 1

HCID 178478704HCID 178478704, compoundYield 45%

Reagents, catalysts & solvents 5

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

Procedure

3-(Naphthalene-1-sulfonyl)-1H-indazol-5-ylamine A mixture of 3-(naphthalen-1-ylsulfanyl)-5-nitro-1H-indazole (5.50 g, 17.11 mmol) and 3-chloroperoxybenzoic acid (17.91 g, 103.80 mmol) in CHCl3 (115 mL) was stirred at room temperature for 4 hr, diluted with EtOAc, washed with Na2SO3 solution, water, brine, dried over Na2SO4, and concentrated in vacuo to effort the crude intermediate which was carried out directly for the next step reaction without further purification. The mixture of the crude sulfone intermediate, tin mossy (15.79 g, 133.01 mmol) in MeOH and conc. hydrochloric acid was heated at 60° C., diluted with CH2Cl2, and neutralized to basic with NaOH or Na2CO3 solution. The aqueous layer was extracted with CH2Cl2. Combined organic layers were dried over Na2SO4 and concentrated in vacuo followed by chromatography purification to provide the title compound (2.50 g, 45% overall yield). MS (ES+) m/e 324 (MH+) Step 4

Workup

  1. washwashed with Na2SO3 solution, water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo to effort the crude intermediate which
  4. customwas carried out directly for the next step reaction without further purification
  5. temperaturewas heated at 60° C.
  6. extractionThe aqueous layer was extracted with CH2Cl2
  7. dry with materialCombined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customfollowed by chromatography purification

Sources & evidence

ORD record
ord-2edb7c82f2554192bda91732644ad443
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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