Water → 63805-96-9

HRID 436760

Reaction equation

HRID 436760 reaction equation
[S-:1][C:2]#[N:3].[Na+].[C:5]([N:9]=[N:10][C:11](Cl)([CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:12])([CH3:8])([CH3:7])[CH3:6].O>C(O)(C)C>[C:5]([N:9]=[N:10][C:11]([N:3]=[C:2]=[S:1])([CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:12])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 516871Sodium thiocyanateHCID 23344796(E)-1-tert-Butyl-2-(2-chloro-4-methylpentan-2-yl)diazene

Product 1

HCID 2143116863805-96-9

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred solution of 26.1 grams (0.3 moles) of sodium thiocyanate in 150 ml of 75% aqueous isopropanol in a 500 ml erlenmeyer flask, cooled to 5° C., was added 61.2 grams (0.3 moles) of 2-t-butylazo- 2-chloro-4-methylpentane holding the reaction temperature at 10°-20° C. After the addition was complete, the reaction mixture was stirred an additional two hours at 30° C., poured into 300 ml water and the product extracted with 200 ml pentane. The pentane extract was washed with water, 10% NaHCO3 solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 55.7 grams (80% crude yield) of a yellow liquid. The product had a strong broad band at 1980- 2080 cm-1 in its infrared spectrum which is indicative of the isothiocyano band.

Workup

  1. additionAfter the addition
  2. extractionthe product extracted with 200 ml pentane
  3. extractionThe pentane extract
  4. washwas washed with water, 10% NaHCO3 solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe pentane evaporated under reduced pressure
  8. customto leave 55.7 grams (80% crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-d5c486a9375c4a3fb176a4ef4a256d07
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Linked notes

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