Water → HCID 21386968, compound

HRID 1834332Notes

Reaction equation

HRID 1834332 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH-].[Na+].[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>CN(C)C=O>[CH:22]1([N:21]=[N:20][C:14]2([N:5]3[C:1](=[O:11])[C:2]4=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]4[C:4]3=[O:6])[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 6809PhthalimideHCID 14798Sodium HydroxideHCID 21387104HCID 21387104, compound

Product 1

HCID 21386968HCID 21386968, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 10.45 grams (.071 moles) phthalimide in 80 mls of N,N-dimethylformamide in a 250 ml 4-neck flask equipped with a magnetic stirrer, thermometer and addition funnel was added 4.0 grams (.05 moles) of 50% sodium hydroxide and the solution stirred for 15 minutes at 40° C. To this solution was added dropwise 11.45 grams (.05 moles) of 1-cyclohexylazo-1chlorocyclohexane (from Example 3-11) over 20 minutes at 40° to 45° C. After the addition was complete, the reaction was stirred an additional 60 minutes at 40° C, poured into 250 ml cold water and the white solid that formed was filtered off and dissolved in 100 ml of pentane. The insolubles were filtered off and the pentane filtrate washed with 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 white solid and weighed 11.5 grams (68% crude yield). The infrared spectrum of the product was in agreement with the structure of 1-cyclohexylazo-1-phthalimidocyclohexane (absence of NH and OH bands and a strong carbonyl band at 1700-1730 cm-1).

Workup

  1. additionthermometer and addition funnel
  2. additionAfter the addition
  3. stirringthe reaction was stirred an additional 60 minutes at 40° C
  4. customthe white solid that formed
  5. filtrationwas filtered off
  6. dissolutiondissolved in 100 ml of pentane
  7. filtrationThe insolubles were filtered off
  8. washthe pentane filtrate washed with water and saturated sodium bicarbonate solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-257fdfb5b7724cb8a637415d89fb9ec2
Source dataset
uspto-grants-1978_01
Patent number
US04069377

Reaction notes

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