Hydrochloric Acid → HCID 18996986, compound

HRID 374640Notes

Reaction equation

HRID 374640 reaction equation
[CH:1]1[CH:6]=[C:5]([OH:7])[C:4]2[C:8]([C:10]3[C:15]([OH:16])=[CH:14][C:13]([CH2:17][OH:18])=[CH:12][C:11]=3[C:19](=[O:20])[C:3]=2[CH:2]=1)=[O:9].Cl>CS(C)=O.C(N(CC)CC)C>[OH:16][C:15]1[C:10]2[C:8](=[O:9])[C:4]3[C:3](=[CH:2][CH:1]=[CH:6][C:5]=3[OH:7])[C:19](=[O:20])[C:11]=2[CH:12]=[C:13]([CH:17]=[O:18])[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10207Aloe-emodin

Product 1

HCID 18996986HCID 18996986, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To aloe-emodin (5.0 g) in dry dimethyl sulphoxide (55 ml) and triethylamine (77 ml) was added a solution/suspension of sulphur trioxide-pyridine complex (29.4 g) in dry dimethyl sulphoxide (100 ml), dropwise with stirring, over 15 minutes. The addition was slightly exothermic and gave a dark brown solution, which was stirred at room temperature for 2-3 hours, then poured onto dilute hydrochloric acid (1000 ml, 0.5M), stirred for 15 minutes, then left to stand for 15 minutes. The suspension was filtered (slow), washed with water (400 ml) and pulled dry to leave a brown solid. Dried at 50° C. in a vacuum oven, m.p. 198°-200° C.

Workup

  1. additionThe addition
  2. customgave a dark brown solution, which
  3. stirringwas stirred at room temperature for 2-3 hours
  4. stirringstirred for 15 minutes
  5. waitleft
  6. waitto stand for 15 minutes
  7. filtrationThe suspension was filtered (slow)
  8. washwashed with water (400 ml)
  9. custompulled dry
  10. customto leave a brown solid
  11. customDried at 50° C. in a vacuum oven, m.p. 198°-200° C.

Sources & evidence

ORD record
ord-13c599ecb62d487e8c0df00fb335ae89
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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