Water → HCID 53761460, compound

HRID 436756Notes

Reaction equation

HRID 436756 reaction equation
[S-:1][C:2]#[N:3].[Na+].[N:5]([C:14](Cl)([CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:15])=[N:6][C:7](Cl)([CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:8].O.[N-:22]=[C:23]=[S:24]>C(O)(C)C.CCCCC>[N:5]([C:14]([N:22]=[C:23]=[S:24])([CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:15])=[N:6][C:7]([N:3]=[C:2]=[S:1])([CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 516871Sodium thiocyanateHCID 53746083Bis(2-chloro-4-methylpentan-2-yl)diazeneHCID 178418790HCID 178418790, compound

Product 1

HCID 53761460HCID 53761460, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8003PentaneSolvent

Procedure

To a stirred solution of 19.2 grams (0.22 moles) of sodium thiocyanate in 120 ml of 75% aqueous isopropanol in a 250 ml erlenmeyer flask was added 26.7 grams (0.1 mole) of 2,2'-azobis(2-chloro-4-methylpentane) (from Example XXIXA) over 40 minutes while holding the temperature below 20° C. with a water bath. After the addition was complete the reaction mixture was stirred an additional 60 minutes at room temperature, poured into 300 ml water and extracted with pentane. The pentane extract was washed with water, 10% NaHCO3 solution, water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave a yellow semi-solid. The semi-solid was slurried in cold pentane and filtered. The filter cake was dried and weighed 8.0 grams (25% crude yield). This material was the undesired 2,2'-azobis(2-thiocyanato-4-methylpentane) and had a sharp band at 2170 cm-1 in its infrared spectrum. The pentane filtrate was stripped under reduced pressure to leave 11.0 grams (34% crude yield) of a yellow liquid. The infrared spectrum of this liquid had a strong broad band at 2000-2130 cm-1 in its infrared spectrum which is indicative of the isothiocyanate isomer.

Workup

  1. customthe temperature below 20° C.
  2. additionAfter the addition
  3. extractionextracted with pentane
  4. extractionThe pentane extract
  5. washwas washed with water, 10% NaHCO3 solution, water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe pentane evaporated under reduced pressure
  9. customto leave a yellow semi-solid
  10. filtrationfiltered
  11. customThe filter cake was dried
  12. customto leave 11.0 grams (34% crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-bc014e968e9c408a8d5d5a0bab5dbda1
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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