1,2-Diiodoethane → HCID 14405318, compound

HRID 477895Notes

Reaction equation

HRID 477895 reaction equation
ClC1[N:3]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:5]C=1.C([Li])CCC.[I:18][CH2:19][CH2:20]I.[Cl-:22].[NH4+]>C(OCC)C>[Cl:22][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[S:5][C:19]([I:18])=[CH:20][N:3]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 122241,2-DiiodoethaneHCID 25517Ammonium ChlorideHCID 15179913HCID 15179913, compoundHCID 178418339Butyllithium

Product 1

HCID 14405318HCID 14405318, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.3 grams (0.012 mole of 2-(4-chloro(phenyl)thiazole in 20 ml of diethyl ether was cooled to -78° C. To this solution was added 4.72 ml of a 2.5 M solution of n-butyllithium in hexanes. This mixture was stirred for 30 minutes. A solution of 3.3 grams (0.012 mole) of 1,2-diiodoethane in 15 ml of diethyl ether was added, and the resultant mixture was allowed to warm to room temperature and stir for approximately 18 hours. Approximately 50 ml of an aqueous, saturated ammonium chloride solution was added, and the resultant mixture was poured into a separatory funnel. The organic phase was washed with water followed by an aqueous, saturated sodium chloride solution. The washed organic phase was dried over anhydrous sodium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride:n-hexane (3:1), to yield 2.6 grams of 2-(4-chlorophenyl)- 5-iodothiazole as a solid.

Workup

  1. stirringstir for approximately 18 hours
  2. washThe organic phase was washed with water
  3. dry with materialThe washed organic phase was dried over anhydrous sodium sulfate
  4. filtrationwas filtered
  5. customThe filtrate was evaporated under reduced pressure
  6. customleaving a residue
  7. customThis residue was purified by column chromatography on silica gel
  8. washeluting with methylene chloride:n-hexane (3:1)

Sources & evidence

ORD record
ord-15e52181ae834ee2853fdc5543acb2cb
Source dataset
uspto-grants-1989_12
Patent number
US04889867

Reaction notes

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