1,3-Benzenediamine, 4-[(4-ethoxyphenyl)azo]-, monohydrochloride → HCID 10034698, compound

HRID 1769241Notes

Reaction equation

HRID 1769241 reaction equation
CC[O:3][C:4]1[CH:5]=[CH:6][C:7](N=NC2C=CC(N)=CC=2N)=[CH:8]C=1.Cl.Cl[C:22]1C=CC=C(C(OO)=O)C=1.[C:32](=[O:35])([O-])[OH:33].[Na+]>C(Cl)Cl>[CH3:22][C:6]1[C@H:7]2[CH2:8][O:35][C@H:32]([O:33]2)[C:4](=[O:3])[CH:5]=1

Participants

5

Reactant 3

HCID 168361,3-Benzenediamine, 4-[(4-ethoxyphenyl)azo]-, monohydrochlorideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 10034698HCID 10034698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The serenium derivative obtained by the above reaction was dissolved in 20 ml of dry methylene chloride under an inert atmosphere of nitrogen gas, and 60 mg of m-chloroperbenzoic acid was added thereto at -78° C. The mixture was stirred for 20 minutes and then a saturated sodium hydrogencarbonate aqueous solution was added. The mixture was extracted twice with methylene chloride. The organic layers were put together and washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained syrup crude product was purified by silica gel thin layer chromatography (methylene chloride) to obtain 1.7 mg of desired 1,6-anhydro-3,4-dideoxy-4-methyl-β-D-glycero-hex-3-enopyranos-2-ulose (Intermediate No. 43) as a colorless transparent liquid. The NMR analytical data of this product are as follows.

Workup

  1. additionwas added
  2. customat -78° C
  3. extractionThe mixture was extracted twice with methylene chloride
  4. washwashed twice with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe obtained syrup crude product was purified by silica gel thin layer chromatography (methylene chloride)

Sources & evidence

ORD record
ord-54a11b5a97da4f819100ece94136c7f5
Source dataset
uspto-grants-1995_01
Patent number
US05380834

Reaction notes

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