Potassium Iodide → 3-Cyanomethyl-4-iodo-benzonitrile

HRID 656503Notes

Reaction equation

HRID 656503 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[CH2:14][C:15]#[N:16].[I-:17].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.S(=O)(=O)(O)O>[C:15]([CH2:14][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:6]=1[I:17])[C:10]#[N:11])#[N:16]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 23668193Sodium NitriteHCID 574685124-Amino-3-cyanomethyl-benzonitrile

Product 1

HCID 574685113-Cyanomethyl-4-iodo-benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Procedure

2 mmol of Sodium nitrite in 5 ml water is added dropwise over 10 minutes to a stirred solution of 2 mmol of 4-amino-3-cyanomethyl-benzonitrile in 6 ml of water and 3 ml of conc. sulphuric acid at 0° C. After a further 15 minutes at 5° C., a solution of 3.9 mmol of potassium iodide in 6 ml of water is quickly added and the mixture allowed to warm to room temperature. 10% Aqueous sodium thiosulphate is added, the mixture is extracted with ethyl acetate, the extract is dried over magnesium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialthe extract is dried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-1ba032169ccd41a887f5d57d763dab81
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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