Potassium Iodide → HCID 515402, compound

HRID 1076907Notes

Reaction equation

HRID 1076907 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:12]1[CH:25]=[CH:24][C:23]2[O:22][C:21]3[C:16](=[CH:17][C:18]([C:26](OCC)([O:31]CC)[CH2:27][CH2:28][CH2:29]Cl)=[CH:19][CH:20]=3)[CH2:15][C:14]=2[CH:13]=1)(OCC)[O:6]CC.[I-].[K+].[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>O1CCCC1>[O:42]1[CH2:43][CH2:44][N:39]([CH2:2][CH2:3][CH2:4][C:5]([C:12]2[CH:25]=[CH:24][C:23]3[O:22][C:21]4[C:16](=[CH:17][C:18]([C:26](=[O:31])[CH2:27][CH2:28][CH2:29][N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)=[O:6])[CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 21538567HCID 21538567, compound

Product 1

HCID 515402HCID 515402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 43.2 g (0.08 mole) 2,7-bis(4-chloro-1,1-diethoxybutyl)xanthene, 2 g. of potassium iodide, 100 ml. of morpholine and 100 ml. tetrahydrofuran was heated for 24 hours with stirring in a Paar bomb at 110°C. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was cooled, dissolved in 300 ml. of 10% HCl and refluxed for 1 hour. The solution was cooled, filtered, the filtrate made alkaline, and extracted with chloroform. The chloroform extract was evaporated to dryness and the residue was recrystallized twice from a 1:4 mixture of benzene in heptane. Upon drying under vacuum, the desired product was obtained. M.P. 110°-111.5°C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. temperatureThe residue was cooled
  5. dissolutiondissolved in 300 ml
  6. temperatureof 10% HCl and refluxed for 1 hour
  7. temperatureThe solution was cooled
  8. filtrationfiltered
  9. extractionextracted with chloroform
  10. extractionThe chloroform extract
  11. customwas evaporated to dryness
  12. customthe residue was recrystallized twice from a 1:4 mixture of benzene in heptane
  13. customUpon drying under vacuum

Sources & evidence

ORD record
ord-d8a3df08ab304dd2ac39bf8aeb83a391
Source dataset
uspto-grants-1976_05
Patent number
US03957989

Reaction notes

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