Sodium Dithionite → HCID 70469103, compound

HRID 128006Notes

Reaction equation

HRID 128006 reaction equation
[OH:1][C:2]1([C:52]([NH2:54])=[O:53])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](=[O:31])[CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH2:24][CH3:25])([CH3:23])[CH3:22])=[CH:17][C:16]=3[C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])[CH:10]=2)[C:5]([N:32]=NC2C=CC(C(O)=O)=CC=2)=[C:4]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:3]1[CH2:49][CH2:50][CH3:51].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[OH:1][C:2]1([C:52]([NH2:54])=[O:53])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](=[O:31])[CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH2:24][CH3:25])([CH3:23])[CH3:22])=[CH:17][C:16]=3[C:26]([CH2:29][CH3:30])([CH3:27])[CH3:28])[CH:10]=2)[C:5]([NH2:32])=[C:4]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:3]1[CH2:49][CH2:50][CH3:51]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 70468821HCID 70468821, compound

Product 1

HCID 70469103HCID 70469103, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 6.15 g of 1-Hydroxy-2-propyl-3-phenyl-4-[(4-carboxy)phenylazo]-7-[(2,4-ditertamyl)phenoxyacetyl]naphthamide prepared in step (7) in 100 ml of ethanol was refluxed under nitrogen with strong stirring. A solution of 6.93 g of sodium hydrosulfite in 36 ml of water was then added. The reaction mixture was stirred for 30 minutes at reflux temperature. After cooling, the reaction mixture was poured into 200 ml of ice water. The organic products were extracted with ethyl ether. The extracts were washed with a sodium bicarbonate saturated aqueous solution and with water. They were finally dried and evaporated to dryness under reduced pressure. After treatment with petroleum ether, the crystals formed were filtered off. The crude product was recrystallized from acetonitrile. The recrystallized product was washed with boiling methanol and with petroleum ether before being dried.

Workup

  1. temperaturewas refluxed under nitrogen with strong stirring
  2. temperatureat reflux temperature
  3. temperatureAfter cooling
  4. extractionThe organic products were extracted with ethyl ether
  5. washThe extracts were washed with a sodium bicarbonate saturated aqueous solution and with water
  6. customThey were finally dried
  7. customevaporated to dryness under reduced pressure
  8. customAfter treatment with petroleum ether, the crystals formed
  9. filtrationwere filtered off
  10. customThe crude product was recrystallized from acetonitrile
  11. washThe recrystallized product was washed with boiling methanol and with petroleum ether
  12. custombefore being dried

Sources & evidence

ORD record
ord-917ed18355bb460bb3dda9dbec78b18c
Source dataset
uspto-grants-1981_03
Patent number
US04258120

Reaction notes

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