Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86596759, compound

HRID 1827320Notes

Reaction equation

HRID 1827320 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][NH:11][CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:13]([C:15]([OH:17])=[O:16])[OH:14])([O-:3])=[O:2].[C:24]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CO[CH:43](OC)[C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=1[O:52][CH3:53].C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH3:24][O:16][C:15]([CH:13]1[O:14][CH:43]([C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=2[O:52][CH3:53])[N:11]([S:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH:12]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 142873251-(Dimethoxymethyl)-2,4-dimethoxybenzeneHCID 22137749HCID 22137749, compound

Product 1

HCID 86596759HCID 86596759, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A hot solution of 6.6 g N-(2-nitrobenzenesulfenyl)-3-phenylisoserine in 100 ml of dry benzene is added with 0.5 g of pyridinium p-toluenesulfonate and 5.3 g of 2,4-dimethoxybenzaldehyde dimethylacetal. The solution is refluxed for 4 hours, then left to cool to room temperature. After that, 10 ml of a NaHCO3 saturated solution are added and the phases are separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried over Na2SO4 and evaporated under reduced pressure. The residual yellow oil is purified by chromatography (silica,hexane-ethyl acetate 5:1 with 2% triethylamine) to give the desired product in 74% yield.

Workup

  1. temperatureThe solution is refluxed for 4 hours
  2. waitleft
  3. customthe phases are separated
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. dry with materialthe combined organic phases are dried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe residual yellow oil is purified by chromatography (silica,hexane-ethyl acetate 5:1 with 2% triethylamine)

Sources & evidence

ORD record
ord-46d723a0ac1c40b2a60a4de374268db4
Source dataset
uspto-grants-2006_05
Patent number
US07053222B2

Reaction notes

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