Water → HCID 21387188, compound

HRID 2398596Notes

Reaction equation

HRID 2398596 reaction equation
[O-:1][C:2]#[N:3].[K+].[CH3:5][CH:6]([N:11]=[N:12][C:13](Br)([CH2:15][CH3:16])[CH3:14])[CH2:7][CH:8]([CH3:10])[CH3:9].O>CC(C)=O>[CH3:5][CH:6]([N:11]=[N:12][C:13]([N:3]=[C:2]=[O:1])([CH2:15][CH3:16])[CH3:14])[CH2:7][CH:8]([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11378442Potassium cyanateHCID 21387239HCID 21387239, compound

Product 1

HCID 21387188HCID 21387188, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3.25 grams (0.04 moles) of potassium cyanate in 75 ml of 70% aqueous acetone in a 125 ml erlenmeyer flask was added 9.4 grams (0.0377 moles) of 2-(1,3-dimethylbutylazo)-2-bromobutane (from Example III) over 5 minutes while holding the reaction temperature at 15°-20° C. with a cold water bath. After the addition was complete the reaction was stirred an additional hour at room temperature, poured into 200 ml of water and the product extracted with 100 ml of pentane. The pentane solution was separated, washed with 50 ml portions of water and saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure on a rotating evaporator. The product was a yellow liquid and weighed 6.4 grams (80.5% crude yield). The infrared spectrum was in agreement with the structure of 2-(1,3-dimethylbutylazo)-2-isocyanatobutane (strong broad isocyanate band at 2125-2225 cm-1).

Workup

  1. customat 15°-20° C.
  2. additionAfter the addition
  3. extractionthe product extracted with 100 ml of pentane
  4. customThe pentane solution was separated
  5. washwashed with 50 ml portions of water and saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-e3a171d839634556903403cb9efacf7b
Source dataset
uspto-grants-1977_05
Patent number
US04025502

Reaction notes

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