Potassium Iodide → HCID 21412250, compound

HRID 259526Notes

Reaction equation

HRID 259526 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:13]2[C:16]3[C:6]=1[CH2:7][CH2:8][C:9]=3[CH:10]=[CH:11][C:12]=2[C:17](=[O:20])[CH2:18]Cl)=[O:4].[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].[I-].[K+]>O1CCCC1>[ClH:1].[ClH:1].[CH2:21]([N:23]([CH2:24][CH3:25])[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:13]2[C:16]3[C:6]=1[CH2:7][CH2:8][C:9]=3[CH:10]=[CH:11][C:12]=2[C:17](=[O:20])[CH2:18][N:23]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:4])[CH3:22]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 21412242HCID 21412242, compound

Product 1

HCID 21412250HCID 21412250, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 30.7 g (0.1 mole) of 3,6-bis(2-chloroacetyl)acenaphthene, 100 ml of diethylamine and 2 g of potassium iodide is dissolved in 500 ml of tetrahydrofuran and allowed to stand in a stoppered flask for 8 days. The resulting amine salt which forms is filtered, washed with tetrahydrofuran and the combined filtrates reduced to dryness in vacuo. The residue is dissolved in methylene chloride, treated with charcoal and acidified using ethereal hydrochloric acid. The resulting solid which forms is filtered, recrystallized from a methanol-ether solution and further recrystallized from a methanol-ethyl acetate solution to yield a product, hygroscopic in nature, which indicated by its analysis to be a tetrahydrate having a m.p. 220.5°-222° C. (dec), λmax(EtOH) 283.

Workup

  1. filtrationThe resulting amine salt which forms is filtered
  2. washwashed with tetrahydrofuran
  3. dissolutionThe residue is dissolved in methylene chloride
  4. additiontreated with charcoal
  5. filtrationThe resulting solid which forms is filtered
  6. customrecrystallized from a methanol-ether solution
  7. customfurther recrystallized from a methanol-ethyl acetate solution
  8. customto yield a product, hygroscopic in nature, which

Sources & evidence

ORD record
ord-830ed16d132e428ab6113795c49e2da3
Source dataset
uspto-grants-1977_07
Patent number
US04038400

Reaction notes

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