Sodium Iodide → HCID 19894518, compound

HRID 892922Notes

Reaction equation

HRID 892922 reaction equation
[I-:1].[Na+].[C:3](=[O:18])([O:8][CH:9]1[CH2:14][CH:13]([CH3:15])[CH2:12][C:11]([CH3:17])([CH3:16])[CH2:10]1)[O:4][CH:5](Cl)[CH3:6]>C(#N)C>[C:3](=[O:18])([O:8][CH:9]1[CH2:14][CH:13]([CH3:15])[CH2:12][C:11]([CH3:17])([CH3:16])[CH2:10]1)[O:4][CH:5]([I:1])[CH3:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19894510HCID 19894510, compound

Product 1

HCID 19894518HCID 19894518, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (250 ml) is warmed to 50° C. and 38 g of sodium iodide is added and dissolved, followed by addition of 14 g of 1-chloroethyl 3,3,5-trimethylcyclohexyl carbonate. The mixture is stirred for 2 hours, poured into 250 ml of ice-water and extracted with two 200-ml portions of ethyl acetate. The extracts are combined, washed with 150 ml of 5% aqueous sodium thiosulfate, 300 ml of water and 300 ml of saturated aqueous sodium chloride (twice) in that order and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure to to give the title compound as oil.

Workup

  1. dissolutiondissolved
  2. extractionextracted with two 200-ml portions of ethyl acetate
  3. washwashed with 150 ml of 5% aqueous sodium thiosulfate, 300 ml of water and 300 ml of saturated aqueous sodium chloride (twice) in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent is then distilled off under reduced pressure

Sources & evidence

ORD record
ord-22d92f34b66643f58eed761bbe868b0d
Source dataset
uspto-grants-1992_06
Patent number
US05120841

Reaction notes

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