Sodium Iodide → HCID 20485542, compound

HRID 647135Notes

Reaction equation

HRID 647135 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5](=[O:8])[CH2:6]Cl.[N:13]1([C:18]2[S:22][S:21][C:20](=[S:23])[CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[I-:24].[Na+]>CC(C)=O>[OH2:1].[I-:24].[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5](=[O:8])[CH2:6][S:23][C:20]1[S:21][S:22][C:18](=[N+:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[CH:19]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 668342-Chloro-3',4'-dihydroxyacetophenoneHCID 13150962HCID 13150962, compound

Product 1

HCID 20485542HCID 20485542, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,4-Dihydroxyphenacyl chloride (7 g) is added to a suspension of 5-(pyrrolidin-1-yl)-1,2-dithiol-3-thione (5.1 g) and sodium iodide (6.2 g) in acetone (90 cc), and the reaction mixture is kept under reflux for 1 hour. After cooling, the insoluble product is filtered off and washed successively with acetone (3×20 cc), with water (3×20 cc) and then with diethyl ether (3×20 cc). By recrystallisation of the resulting product from a dimethylformamide/methanol mixture (20/80 by volume; 600 cc) and then desolvation by stirring for 30 minutes in water (100 cc), N-[5-(3,4-dihydroxyphenacylthio)-1,2-dithiol-3-ylidene]-pyrrolidinium iodide hydrate (6.9 g), melting at about 130° C., is obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe insoluble product is filtered off
  4. washwashed successively with acetone (3×20 cc), with water (3×20 cc)
  5. customBy recrystallisation of the resulting product from a dimethylformamide/methanol mixture (20/80 by volume; 600 cc)

Sources & evidence

ORD record
ord-84b06199db3b4e80a761d4c9159decf0
Source dataset
uspto-grants-1983_10
Patent number
US04407797

Reaction notes

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