Water → HCID 21431177, compound

HRID 436754Notes

Reaction equation

HRID 436754 reaction equation
[S-:1][C:2]#[N:3].[Na+].[C:5]([N:9]=[N:10][C:11](Cl)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[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])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 516871Sodium thiocyanateHCID 2334477457908-73-3

Product 1

HCID 21431177HCID 21431177, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 26.0 grams (0.32 moles) of sodium thiocyanate in 150 ml of 75% aqueous isopropanol cooled to 5° C. in a 500 ml erlenmeyer flask was added 71.4 grams (0.32 moles) of 1-t-butylazo-1-chloro-1-phenylethane over 3 minutes holding the temperature at 5°-10° C. with an ice bath. The reaction mixture was stirred for 90 minutes at room temperature, poured into 300 ml water and the product extracted with 100 ml of pentane. The pentane extract was washed twice with 100 ml water, once with 10% NaHCO3 solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure. The product was a light brown liquid which weighed 43.3 grams (54.6% crude yield). The infrared spectrum of the product had a very strong broad band at 1960-2175 cm-1 which is indicative of the α-isothiocyanate.

Workup

  1. customat 5°-10° C.
  2. extractionthe product extracted with 100 ml of pentane
  3. extractionThe pentane extract
  4. washwas washed twice with 100 ml water, once with 10% NaHCO3 solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe pentane evaporated under reduced pressure

Sources & evidence

ORD record
ord-f9157204589340058f7504b024d8f403
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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