Sodium Iodide → HCID 21541508, compound

HRID 268110Notes

Reaction equation

HRID 268110 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH:16](C(=O)C)[CH2:15][CH:14](C(=O)C)[CH:13]1[C:23]#[N:24])([O:3][CH2:4][CH3:5])=[O:2].ClC1C=CC=[C:28]([C:32]([O:34]O)=[O:33])C=1.[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH:16]([O:3][C:1](=[O:2])[CH3:6])[CH2:15][CH:14]([O:34][C:32](=[O:33])[CH3:28])[CH:13]1[C:23]#[N:24])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21553461HCID 21553461, compound

Product 1

HCID 21541508HCID 21541508, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Five hundred milligrams of 2-(6'-carboethoxyhexyl)-3,5-diacetyl-cyclopentanecarbonitrile and 600 mg of meta-chloroperbenzoic acid were dissolved in 30 ml of chloroform, and the solution was allowed to stand for 4 days at room temperature. The reaction mixture was then treated with a 5% solution of sodium iodide and then with a 10% solution of sodium thiosulfate. Five hundred (500) milligrams of the resulting oily substance was purified by chromatography on silica gel to yield 200 mg of 2-(6'-carboethoxyhexyl)-3,5-diacetoxy-cyclopentanecarbonitrile which has the following characteristics: Infrared absorption (film method): 2250, 1735, 1235, 1180; Nuclear magnetic resonance (in CDCL3 solvent): the absorption of the methyne protons at the 3- and 5-position were observed at about 4.9 and about 5.2; 4.10 (2H, multiplet signal), 2.05 (6H, two singlet signals acetoxymethyl proton).

Workup

  1. customFive hundred (500) milligrams of the resulting oily substance was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-98c7c6bc02c34408987f49feabc0abd9
Source dataset
uspto-grants-1976_03
Patent number
US03946065

Reaction notes

Loading…