Water → HCID 373155, compound

HRID 436740Notes

Reaction equation

HRID 436740 reaction equation
[O-:1][C:2]#[N:3].[K+].CCCCC.[C:10]([N:14]=[N:15][C:16](Cl)([CH3:18])[CH3:17])([CH3:13])([CH3:12])[CH3:11].O>C(O)(C)C>[C:10]([N:14]=[N:15][C:16]([N:3]=[C:2]=[O:1])([CH3:18])[CH3:17])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8003PentaneHCID 11378442Potassium cyanateHCID 1564434955296-56-5

Product 1

HCID 373155HCID 373155, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of 40.5 grams (0.5 moles) of potassium cyanate in 250 ml of 75% aqueous isopropanol in a 2 liter jacketed reactor, cooled to 5° C., was added the above pentane solution of 2-t-butylazo-2-chloropropane over 15 minutes, holding the reaction temperature at 10°-20° C. After the addition was complete, the reaction mixture was stirred an additional 2 hours at room temperature, 500 ml of water added and the reaction stirred until the salts dissolved. The pentane layer was separated, washed with 250 ml water, 250 ml 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave 59.6 grams (70% overall crude yield) of a yellow liquid. The product had a strong broad band at 2225 cm-1 in its infrared spectrum.

Workup

  1. customat 10°-20° C
  2. additionAfter the addition
  3. stirringthe reaction stirred until the salts
  4. dissolutiondissolved
  5. customThe pentane layer was separated
  6. washwashed with 250 ml water, 250 ml 10% NaHCO3 solution
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customthe pentane evaporated under reduced pressure
  10. customto leave
  11. custom59.6 grams (70% overall crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-17132dcfd99a4639b87901454c173e10
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

Loading…