2-Iodobutane → HCID 4638247, compound

HRID 1733151Notes

Reaction equation

HRID 1733151 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[OH-].[Na+].I[CH:13]([CH2:15][CH3:16])[CH3:14]>C(#N)C>[CH:13]([N:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1]1)([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 105592-IodobutaneHCID 14798Sodium HydroxideHCID 178418385HCID 178418385, compound2×

Product 1

HCID 4638247HCID 4638247, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 96.0 grams of benzotriazole in 800 milliliters of acetonitrile at 50° C. is added 33.6 grams of sodium hydroxide pels. After most of the sodium hydroxide has reacted with the benzotriazole, 190 grams of 2-iodobutane is added in one portion and the resulting solution is refluxed for 15 hours. The acetonitrile is then evaporated and 300 milliliters of concentrated hydrochloric acid is added to the residual oil followed by the addition of 800 milliliters of benzene. The precipitated sodium iodide is removed by filtration. The acid layer is separated from the benzene layer and then washed three more times with 300 milliliters of benzene. The benzene washings are combined, dried over MgSO4 and evaporated to yield 48 grams (34%) of the 2-sec-butyl-2H-benzotriazole as an oil. The material is purified by distillation, b.p. 0.25 mm Hg=63° C.

Workup

  1. additionis added in one portion
  2. temperaturethe resulting solution is refluxed for 15 hours
  3. customThe acetonitrile is then evaporated
  4. addition300 milliliters of concentrated hydrochloric acid is added to the residual oil
  5. additionfollowed by the addition of 800 milliliters of benzene
  6. customThe precipitated sodium iodide is removed by filtration
  7. customThe acid layer is separated from the benzene layer
  8. washwashed three more times with 300 milliliters of benzene
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-fc603655cfa64a7386445765e197a1b0
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

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