Water → HCID 21386991, compound

HRID 2398591Notes

Reaction equation

HRID 2398591 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]([N:8]=[N:9][C:10]1(Cl)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:7])[CH3:6].O>CO>[CH:5]([N:8]=[N:9][C:10]1([N:1]=[N+:2]=[N-:3])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 21387085HCID 21387085, compound

Product 1

HCID 21386991HCID 21386991, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 9.75 grams (0.15 moles) of sodium azide in 100 mls of 70% aqueous methanol in a 250 ml erlenmeyer flask cooled in an ice bath, was added 18.85 grams (0.1 moles) of 1-isopropylazo-1-chlorocyclohexane (from Example 3-2) over 15 minutes while holding the reaction temperature below 10° C. After the addition was complete the mixture was stirred an additional 20 minutes at room temperature, poured into 200 ml water and extracted into 100 ml of pentane. The pentane solution was washed successively with 50 ml portions of 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 and weighed 18.4 grams (94.4 % crude yield). It was not shock sensitive and its infrared spectrum was in agreement with the structure of 1-isopropylazo-1-azidocylohexane (strong azide band at 2100 cm-1).

Workup

  1. customthe reaction temperature below 10° C
  2. additionAfter the addition
  3. extractionextracted into 100 ml of pentane
  4. washThe pentane solution was washed successively with 50 ml portions of water and saturated sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-e74b85b54a814258a0c2a4e4b0aa060e
Source dataset
uspto-grants-1977_05
Patent number
US04025502

Reaction notes

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