Hydrochloric Acid → HCID 22890467, compound

HRID 896749Notes

Reaction equation

HRID 896749 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([OH:14])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH3:13])[CH3:3].[C:15]([CH2:17][NH:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])#N.[N+](C1C=CC=CC=1)([O-])=[O:26]>[Cl-].[Zn+2].[Cl-]>[CH2:2]([O:4][C:5]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:8]([C:15](=[O:26])[CH2:17][NH:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])=[C:7]([OH:14])[CH:6]=1)[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 144503103,4-DiethoxyphenolHCID 22890470HCID 22890470, compound

Product 1

HCID 22890467HCID 22890467, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Nitrobenzene (100 ml) was cooled to zero degrees Celsius and saturated with HCl gas. To this solution was added of 3,4-diethoxy-phenol (11.64 g, 64 mmoles), propane-1-sulfonic acid cyanomethyl-amide (10.36 g, 64 mmoles) and zinc chloride (17.45 g, 128 mmoles). The reaction was stirred for 1 hour at zero degrees Celsius and then allowed to warm to room temperature. Stirring was continued for 2 hours. Thin-layer chromatography showed consumption of 3,4-diethoxy-phenol. Water (100 ml) was added cautiously and the reaction was heated to 100 degrees Celsius for 1 hour. The reaction was cooled, and extracted with methylene chloride. The extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed in vacuo. The residue was submitted to flash chromatography (2.5-5% ethyl acetate in methylene chloride). The purified product was triturated with ether, filtered and air dried to yield 17.3 g of propane-1-sulfonic acid [2-(4,5-diethoxy-2-hydroxy-phenyl)-2-oxo-ethyl]-amide. 1HNMR (CDCl3): 11.86 (s, 1H), 6.93 (s, 1H), 6.46 (s, 1H), 5.26 (t, 1H), 4.55 (d, 2H), 4.14 (q, 2H), 4.03 (q, 2H), 3.05 (m, 2H), 1.90 (m, 2H), 1.45 (m, 6H), 1.07 (t, 3H).

Workup

  1. stirringStirring
  2. waitwas continued for 2 hours
  3. customconsumption of 3,4-diethoxy-phenol
  4. additionWater (100 ml) was added cautiously
  5. temperaturethe reaction was heated to 100 degrees Celsius for 1 hour
  6. temperatureThe reaction was cooled
  7. extractionextracted with methylene chloride
  8. washThe extracts were washed with water, brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was removed in vacuo
  12. customThe purified product was triturated with ether
  13. filtrationfiltered
  14. customair dried

Sources & evidence

ORD record
ord-077dbf38399c487e8b12513be6911fb5
Source dataset
uspto-grants-2005_07
Patent number
US06919369B2

Reaction notes

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