Water → HCID 70623127, compound

HRID 1834328Notes

Reaction equation

HRID 1834328 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH:14]1([N:20]=[N:21][C:22]2(Cl)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.O>CO>[CH:22]1([N:21]=[N:20][C:14]2([S:13][C:10]3[CH:9]=[CH:8][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[CH:12][CH:11]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 754544-Tert-ButylbenzenethiolHCID 21387104HCID 21387104, compound

Product 1

HCID 70623127HCID 70623127, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4.96 grams (0.062 moles) of 50% sodium hydroxide in 100 ml of methanol in a 250 ml erlenmeyer flask was added 10.45 grams (0.063 moles) of para-(t-butyl)-thiophenol and the solution stirred for 15 minutes at room temperature. The solution was cooled to 5° C and 13.7 grams (.06 moles) of 1-cyclohexylazo-1-chlorocyclohexane (from Example 3-11) was added dropwise over 20 minutes while holding the reaction temperature at 5° to 10° C with a cold water bath. After the addition was complete the bath was removed and the reaction stirred for an additional 60 minutes at room temperature. A 1.0 gram portion of 50% sodium hydroxide was then added to react with any excess thiophenol, the reaction mixture poured into 300 ml water and the product extracted into 100 ml of pentane. The pentane solution was separated and successively washed with 50 ml portions of water, 10% HCl, water, 5% sodium hydroxide 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 that weighed 14.0 grams (63% crude yield). The infrared spectrum of the product was in agreement with the structure of 1-cyclohexylazo-1-[para-(t-butyl)-thiophenoxy] cyclohexane.

Workup

  1. temperatureThe solution was cooled to 5° C
  2. customat 5° to 10° C
  3. additionAfter the addition
  4. customwas removed
  5. stirringthe reaction stirred for an additional 60 minutes at room temperature
  6. additionA 1.0 gram portion of 50% sodium hydroxide was then added
  7. customto react with any excess thiophenol
  8. extractionthe product extracted into 100 ml of pentane
  9. customThe pentane solution was separated
  10. washsuccessively washed with 50 ml portions of water, 10% HCl, water, 5% sodium hydroxide and saturated sodium bicarbonate solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-adfff903176846989d3190034d86b617
Source dataset
uspto-grants-1978_01
Patent number
US04069377

Reaction notes

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