Potassium Iodide → HCID 21538575, compound

HRID 1076910Notes

Reaction equation

HRID 1076910 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19](=[O:22])[CH2:20]Cl)=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)=[O:4].[I-].[K+].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>O1CCCC1>[OH2:4].[ClH:1].[ClH:1].[O:28]1[CH2:29][CH2:30][N:25]([CH2:2][C:3]([C:5]2[CH:18]=[CH:17][C:16]3[O:15][C:14]4[C:9](=[CH:10][C:11]([C:19](=[O:22])[CH2:20][N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[CH:12][CH:13]=4)[CH2:8][C:7]=3[CH:6]=2)=[O:4])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 12340276HCID 12340276, compound

Product 1

HCID 21538575HCID 21538575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 22.7 g (0.068 mole) of 2,7-bis(chloroacetyl)-xanthene, 2 g of potassium iodide, 200 ml. of morpholine and 500 ml. of tetrahydrofuran was allowed to stand for 7 days at room temperature, then filtered. The filtrate was evaporated to dryness and the resulting residue was cooled, dissolved in dilute HCl and filtered. The filtrate was made alkaline and the product was extracted with methylene chloride. The methylene chloride extract was evaporated to a small volume, cooled and acidified to Congo Red with ethereal HCl. The precipitate was filtered off and recrystallized three times from methanoldiethyl ether. After drying in vacuo and hydrating in a constant humidity chamber, the desired product was obtained. M.P. > 350°C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. temperaturethe resulting residue was cooled
  4. dissolutiondissolved in dilute HCl
  5. filtrationfiltered
  6. extractionthe product was extracted with methylene chloride
  7. extractionThe methylene chloride extract
  8. customwas evaporated to a small volume
  9. temperaturecooled
  10. filtrationThe precipitate was filtered off
  11. customrecrystallized three times from methanoldiethyl ether
  12. customAfter drying in vacuo and hydrating in a constant humidity chamber

Sources & evidence

ORD record
ord-8ffeb46b409f4a51bdaa43b34f83868f
Source dataset
uspto-grants-1976_05
Patent number
US03957989

Reaction notes

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