Sulfuric Acid → HCID 21387012, compound

HRID 2398600Notes

Reaction equation

HRID 2398600 reaction equation
S(=O)(=O)(O)[OH:2].[CH:6]([N:9]=[N:10][C:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:8])[CH3:7]>>[CH:6]([N:9]=[N:10][C:11]1([C:17](=[O:2])[NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 21387098HCID 21387098, compound

Product 1

HCID 21387012HCID 21387012, compound

Conditions

Temperature
25 °C

Procedure

To 100 ml of 96% sulfuric acid cooled to 0° C. in an ice bath was added 13.5 grams (0.0755 moles) of 1-isopropylazo-1-cyanocyclohexane (from Example 4-b-6) dropwise over 1/2 hour while holding the temperature at 0° C. After the addition was complete the temperature was allowed to rise to 10° C. over 1/2 hour and to 25° C. over another 1/2 hour and then stirred another 1/2 hour at 25° C. The reaction mixture was poured onto 1/2 liter of ice and stirred until all of the ice dissolved. A white solid that formed was filtered off and the aqueous acid filtrate was extracted with 200 ml of methylene chloride. The methylene chloride extract was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated under reduced pressure on a rotating evaporator. The product was a light brown liquid and weighed 5.0 grams (33.7% crude yield). The infrared spectrum of the product was in agreement with the structure of 1-isopropylazo-1-carbamylcyclohexane (strong broad carbonyl band at 1675-1750 cm-1 and NH band at 3500 cm-1).

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. dissolutiondissolved
  4. customA white solid that formed
  5. filtrationwas filtered off
  6. extractionthe aqueous acid filtrate was extracted with 200 ml of methylene chloride
  7. extractionThe methylene chloride extract
  8. washwas washed with saturated sodium bicarbonate solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe methylene chloride evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-6db4cc2ef08e48b7b3b5d72afa1817a4
Source dataset
uspto-grants-1977_05
Patent number
US04025502

Reaction notes

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