Potassium Iodide → HCID 21559689, compound

HRID 1578637Notes

Reaction equation

HRID 1578637 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20](=[O:24])[CH2:21][CH2:22]Cl)[CH:14]=3)[S:9][C:8]=2[CH:7]=1)=[O:5].[I-].[K+].[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28]>O1CCCC1>[ClH:1].[ClH:1].[CH2:27]([N:29]([CH2:30][CH3:31])[CH2:2][CH2:3][C:4]([C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20](=[O:24])[CH2:21][CH2:22][N:29]([CH2:30][CH3:31])[CH2:27][CH3:28])[CH:14]=3)[S:9][C:8]=2[CH:7]=1)=[O:5])[CH3:28]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 21559677HCID 21559677, compound

Product 1

HCID 21559689HCID 21559689, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 22.4 g (0.03 mole) 2,7-bis(3-chloropropionyl)phenoxathiin, 1 g of potassium iodide, 75 ml of diethylamine and 75 ml of tetrahydrofuran is allowed to stand for 3 days then filtered and the filtrate evaporated to dryness. The residue is dissolved in ethanol and acidified with etheral HCl to Congo Red. The solution is diluted with ethyl ether and the solid filtered off. The solid is thrice dissolved in methanol, filtered, precipitated with ethyl ether and filtered. The resulting product is dried to give 2,7-bis(3-diethylaminopropionyl)phenoxathiin dihydrochloride. M.P. 189°-190°C.

Workup

  1. filtrationthen filtered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue is dissolved in ethanol
  4. additionThe solution is diluted with ethyl ether
  5. filtrationthe solid filtered off
  6. dissolutiondissolved in methanol
  7. filtrationfiltered
  8. customprecipitated with ethyl ether
  9. filtrationfiltered
  10. customThe resulting product is dried

Sources & evidence

ORD record
ord-e05d5e0d0ab84956b7e35a7ca82ed820
Source dataset
uspto-grants-1976_02
Patent number
US03937835

Reaction notes

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