Acetone → Diisopropylether hexane

HRID 1414019Notes

Reaction equation

HRID 1414019 reaction equation
C[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N+]#[C-].C(#N)C.ClCl.[N-]=[N+]=[N-].[Na+].[CH3:20][C:21]([CH3:23])=[O:22]>O>[CH:21]([O:22][CH:6]([CH3:7])[CH3:8])([CH3:23])[CH3:20].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 5

HCID 180AcetoneHCID 6342AcetonitrileHCID 24526ChlorineHCID 33557Sodium AzideHCID 42121842,4-Dimethylphenylisocyanide

Product 1

HCID 21881879Diisopropylether hexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,4-dimethylphenylisonitrile (Ugi, et al., Angew. Chem. Internat. Ed. (Engl.) 4, 472 (1965)) (14.8 g., 0.11 mole) in 100 ml. of acetonitrile was stirred at ice bath temperature while chlorine gas was bubbled in. When tlc indicated that the isonitrile had been consumed, the solvent was removed in vacuo, leaving 22.7 g. of the oily isocyanodichloride. To a solution of the latter in 130 ml. of acetone was added a solution of 7.3 g. (0.11 mole) of sodium azide in 25 ml. of water. After one hour, the acetone was evaporated in vacuo and the aqueous residue was extracted with ethyl acetate. The extract was washed with water and brine, dried (Na2SO4) and evaporated to provide 24.5 g. of a waxy solid. Trituration with isopropyl ether-hexane gave 18.9 g. of the chlorotetrazole, m.p. 75°-77°.

Workup

  1. customwas bubbled in
  2. customhad been consumed
  3. customthe solvent was removed in vacuo
  4. customleaving 22.7 g
  5. customthe acetone was evaporated in vacuo
  6. extractionthe aqueous residue was extracted with ethyl acetate
  7. washThe extract was washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto provide 24.5 g

Sources & evidence

ORD record
ord-7447a8a9753743b7ae781b297dac3b55
Source dataset
uspto-grants-1981_02
Patent number
US04252815

Reaction notes

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