Methane → HCID 12109364, compound

HRID 2116548Notes

Reaction equation

HRID 2116548 reaction equation
[CH2:1]([NH:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[O:12][C:13]1[CH:14]=[C:15]([Cl:19])[CH:16]=[N:17][CH:18]=1)[CH3:2].[I:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.N1C=CC=CC=1.C>C(Cl)Cl.C(OCC)(=O)C.CO>[CH2:1]([NH:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([NH:11][S:28]([C:25]2[CH:26]=[CH:27][C:22]([I:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH:8]=[CH:7][C:6]=1[O:12][C:13]1[CH:14]=[C:15]([Cl:19])[CH:16]=[N:17][CH:18]=1)[CH3:2]

Participants

8

Reactant 4

HCID 297MethaneHCID 1049PyridineHCID 73994-Iodobenzenesulfonyl chlorideHCID 12109363HCID 12109363, compound

Product 1

HCID 12109364HCID 12109364, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-ethyl 5-amino-2-(3-chloro-5-pyridyloxy)benzamide from Example 17.3 (0.9 g) in methylene chloride (10 mL) was added 4-iodobenzenesulfonyl chloride (1.03 g), followed by pyridine (275 μL). The reaction progress was monitored by TLC, and upon completion the solvent was removed under vacuum. The resulting residue was partitioned between methylene chloride and water. The organic layer was drawn off and concentrated to form pink crystals. The crystals were dissolved in ethyl acetate (200 mL) and methanol (10 mL), and decolorized with activated charcoal. After filtration, the solution was concentrated to an oil and the residue was triturated with ether to provide 1.26 g of the title compound as colorless crystals. mp 154-156° C.

Workup

  1. customupon completion the solvent was removed under vacuum
  2. customThe resulting residue was partitioned between methylene chloride and water
  3. concentrationconcentrated
  4. customto form pink crystals
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated to an oil
  7. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-c3b87482b4f54d63ae06a4e80af47fae
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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