Water → HCID 20484071, compound

HRID 648002Notes

Reaction equation

HRID 648002 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][C:15]#[N:16])(=O)=O.[I-:17].[Na+].CCCCCC.C(OCC)(=O)C.O>C(#N)C>[I:17][CH2:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][C:15]#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 12795072HCID 12795072, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 20484071HCID 20484071, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 8 g. of 1-(3-methansulfonyloxypropyl)pyrrol-2-acetonitrile (0.33 moles) in dry acetonitrile (270 ml.) containing dry sodium iodide (12.2 g., 0.081 moles) is stirred under reflux for 40 min. (t.l.c., silica gel, hexane-ethyl acetate, 1:1). The reaction is cooled to 40°, water (50 ml.) is added, and the solvent is then removed in vacuo almost to dryness. To the residue is added saturated sodium chloride solution (300 ml.) and dichloromethane (350 ml.). The organic phase is separated combined with the dichloromethane extracts of the aqueous phase (3×150 ml.), and washed successively with saturated sodium chloride solution, saturated sodium sulfite solution (once) and dilute sodium chloride solution. The solution is dried with sodium sulfate and evaporated in vacuo giving 1-(3-iodopropyl)pyrrol-2-acetonitrile which is an oil (7.7 g) having the following characteristics:

Workup

  1. temperatureThe reaction is cooled to 40°
  2. customthe solvent is then removed in vacuo almost to dryness
  3. additionTo the residue is added saturated sodium chloride solution (300 ml.) and dichloromethane (350 ml.)
  4. customThe organic phase is separated
  5. washwashed successively with saturated sodium chloride solution, saturated sodium sulfite solution (once) and dilute sodium chloride solution
  6. dry with materialThe solution is dried with sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-77ceb1ae49504776ba1a1d4e1e80ad8e
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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