Potassium Iodide → HCID 86733456, compound

HRID 1076909Notes

Reaction equation

HRID 1076909 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+].[CH3:25][NH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCCC1>[OH2:4].[ClH:1].[ClH:1].[CH3:25][N:26]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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][N:26]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[CH3:25])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 7514N-MethylcyclohexylamineHCID 12340276HCID 12340276, compound

Product 1

HCID 86733456HCID 86733456, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 33.5 g (0.1 mole) of 2,7-bis(2-chloroacetyl)-xanthene, 2 g of potassium iodide, 50.6 g (0.5 mole) of N-methylcyclohexylamine and 500 ml. of tetrahydrofuran was allowed to stand for seven days at room temperature, then filtered. The filtrate was evaporated to dryness, and the residue was cooled, then dissolved in 5% HCl and filtered. The filtrate was made alkaline and the product was extracted with methylene chloride, evaporated to a small volume, cooled, and acidified with ethereal HCl to Congo Red. The solid was filtered off and recrystallized four times from methanol-diethyl ether. After drying in vacuo and hydrating in a constant humidity chamber, the desired product was obtained. M.P. 203°-206°C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. temperaturethe residue was cooled
  4. dissolutiondissolved in 5% HCl
  5. filtrationfiltered
  6. extractionthe product was extracted with methylene chloride
  7. customevaporated to a small volume
  8. temperaturecooled
  9. filtrationThe solid was filtered off
  10. customrecrystallized four times from methanol-diethyl ether
  11. customAfter drying in vacuo and hydrating in a constant humidity chamber

Sources & evidence

ORD record
ord-a6e2a0905d044e04ada9da55a9025003
Source dataset
uspto-grants-1976_05
Patent number
US03957989

Reaction notes

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