Water → HCID 69223884, compound

HRID 747632Notes

Reaction equation

HRID 747632 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][CH2:23][CH2:24][OH:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH2:26][C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[F:34])[CH:3]=1.I([O-])(=O)(=O)=[O:36].[Na+].O>C(#N)C.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])[CH2:22][CH2:23][C:24]([OH:36])=[O:25])=[C:4]([CH2:26][C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[F:34])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 58941346HCID 58941346, compound

Product 1

HCID 69223884HCID 69223884, compoundYield 115.8%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To 2.63 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-N-(3-hydroxypropyl)-3,4-dimethoxybenzenesulfonamide (Example 37) dissolved in 35 ml of acetonitrile are added, at room temperature, 0.069 g of ruthenium trichloride, 1.65 g of sodium periodate and 2.7 ml of water. The mixture is left for 10 hours at room temperature. The reaction medium is filtered through talc and then concentrated. The residue is taken up in dichloromethane and washed with 1M hydrochloric acid solution. The organic phase is dried over anhydrous sodium sulfate and concentrated to give 3.13 g of the expected product.

Workup

  1. additionare added, at room temperature
  2. filtrationThe reaction medium is filtered through talc
  3. concentrationconcentrated
  4. washwashed with 1M hydrochloric acid solution
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ac2fba6f5b49a58a5461d63637108e
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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