Benzaldehyde → HCID 86733767, compound

HRID 918565Notes

Reaction equation

HRID 918565 reaction equation
[CH2:1]([C:15]1[C:16]([CH2:23][OH:24])=[C:17]([OH:22])[C:18]([CH3:21])=[N:19][CH:20]=1)[S:2][S:3][CH2:4][C:5]1[C:6]([CH2:13][OH:14])=[C:7]([OH:12])[C:8]([CH3:11])=[N:9][CH:10]=1.[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CCOCC>[CH2:4]([C:5]1[CH:10]=[N:9][C:8]([CH3:11])=[C:7]2[O:12][CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:14][CH2:13][C:6]=12)[S:3][S:2][CH2:1][C:15]1[CH:20]=[N:19][C:18]([CH3:21])=[C:17]2[O:22][CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:24][CH2:23][C:16]=12

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14190Pyrithioxine

Product 1

HCID 86733767HCID 86733767, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.01 moles of 5,5'-(dithiodimethylene) bis[3-hydroxy-4-hydroxymethyl-2-methylpyridine] and 100 ml. of benzaldehyde was saturated with hydrogen chloride gas at 0°-5° and then stirred at this temperature for 4 hours. At this time 800 ml. of ether were added and the resulting precipitate was separated by filtration. This solid was then added to a well stirred mixture of 200 ml. chloroform and 200 ml. of water containing 20 gm. of sodium carbonate. After 15 minutes the chloroform layer was removed, dried, and concentrated to give an oil which gradually solidified. This solid was filtered with the aid of a small amount of ether to give 5,5'-(dithiodimethylene)bis[8-methyl-2-phenyl-4H-m-dioxino[4,5-c]pyridine].

Workup

  1. customthe resulting precipitate was separated by filtration
  2. additionThis solid was then added to a well
  3. stirringstirred
  4. additionmixture of 200 ml
  5. customAfter 15 minutes the chloroform layer was removed
  6. customdried
  7. concentrationconcentrated
  8. customto give an oil which
  9. filtrationThis solid was filtered with the aid of a small amount of ether

Sources & evidence

ORD record
ord-b8c1d02538654848a7effc2ae83de1f8
Source dataset
uspto-grants-1976_07
Patent number
US03971797

Reaction notes

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