Water → HCID 21387152, compound

HRID 2398589Notes

Reaction equation

HRID 2398589 reaction equation
[OH-].[Na+].[SH:3][CH2:4][CH2:5][OH:6].[CH:7]([N:10]=[N:11][C:12]1(Cl)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:9])[CH3:8].O>CO>[CH:7]([N:10]=[N:11][C:12]1([S:3][CH2:4][CH2:5][OH:6])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 15672-MercaptoethanolHCID 14798Sodium Hydroxide2×HCID 21387085HCID 21387085, compound

Product 1

HCID 21387152HCID 21387152, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred solution of 4.8 grams (.06 moles) of 50% sodium hydroxide in 60 ml of methanol in a 125 ml erlenmeyer flask was added 5.46 grams (.07 moles) of 2-mercaptoethanol while holding the reaction temperature below 25° C. After the addition was complete, the mixture was stirred for 20 minutes at 10° C. and 9.5 grams (0.05 moles) of 1-isopropylazo-1-chlorocyclohexane (from Example 3-2) was added dropwise over 25 minutes while holding the temperature below 15° C. After the addition was complete, the reaction was stirred an additional 60 minutes at 5° to 15° C. A .02 mole portion of 50% sodium hydroxide was added, the reaction stirred an additional 10 minutes, poured into 200 ml of water and the product extracted into 100 ml of pentane. The pentane solution was separated and washed successively with 50 ml portions of 5% HCl, 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 weighing 8.5 grams (74% crude yield). The infrared spectrum was in agreement with the structure of 1-isopropylazo-1-(β-hydroxyethylthio)cyclohexane (absence of carbon-chlorine band at 800-825 cm-1 and presence of a strong OH band at 3325 cm-1.)

Workup

  1. customthe reaction temperature below 25° C
  2. additionAfter the addition
  3. customthe temperature below 15° C
  4. additionAfter the addition
  5. stirringthe reaction was stirred an additional 60 minutes at 5° to 15° C
  6. stirringthe reaction stirred an additional 10 minutes
  7. extractionthe product extracted into 100 ml of pentane
  8. customThe pentane solution was separated
  9. washwashed successively with 50 ml portions of 5% HCl, water and saturated sodium bicarbonate solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-c7daad711a19440598b1e616092959c9
Source dataset
uspto-grants-1977_05
Patent number
US04025502

Reaction notes

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