Isopropyl iodide → HCID 20487614, compound

HRID 1447924Notes

Reaction equation

HRID 1447924 reaction equation
[OH-].[Na+].[F:3][C:4]([F:16])([F:15])[S:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.I[CH:18]([CH3:20])[CH3:19]>C1C=CC=CC=1>[CH:18]([CH:12]([C:9]1[CH:8]=[CH:7][C:6]([S:5][C:4]([F:15])([F:3])[F:16])=[CH:11][CH:10]=1)[C:13]#[N:14])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 27779054-(Trifluoromethylthio)phenylacetonitrile

Product 1

HCID 20487614HCID 20487614, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Fifty percent sodium hydroxide (13.5 ml) is added over a 30-minute period dropwise to a suspension of 4-trifluoromethylthiophenylacetonitrile (9.7 g, 0.045 mol), 2-iodopropane (9.5 g, 0.056 mol), and 18 crown-6 (0.61 g, 0.0023 mol) in 13.5 ml of benzene and the exotherm reaches 43° C. After stirring 2.5 hours at ambient temperature, an aliquot placed on glc shows none of the starting nitrile remaining. The reaction is worked up by adding ice water and extracting with ether, which is washed with 10% HCl, water, and dried over sodium sulfate. Evaporation in vacuo gave 10.2 g (86.8%) of a red-brown oil.

Workup

  1. customthe exotherm reaches 43° C
  2. extractionextracting with ether, which
  3. washis washed with 10% HCl, water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-d277342bd76442bda28b856eef841bf9
Source dataset
uspto-grants-1979_12
Patent number
US04178460

Reaction notes

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