Isopropanol → HCID 21431325, compound

HRID 436769Notes

Reaction equation

HRID 436769 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[H-].[Na+].[C:7]([N:11]=[N:12][C:13]1([N:19]=[C:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:10])([CH3:9])[CH3:8].[N-]=C=O>O>[C:7]([N:11]=[N:12][C:13]1([NH:19][C:20]([O:4][CH:1]([CH3:3])[CH3:2])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 105034IsocyanateHCID 214311721-t-Butylazo-1-isocyanatocyclohexane2×

Product 1

HCID 21431325HCID 21431325, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of isopropanol in a 125 ml erlenmeyer flask stirred with a magnetic stirrer, was slowly added 2.1 grams (0.05 moles) of 57% sodium hydride. After the temperature came back to 25° C., 10.5 grams (0.05 moles) of 1-t-butylazo-1isocyanatocyclohexane was added dropwise over 5 minutes. After the addition was complete, the reaction was stirred an additional 30 minutes at room temperature. Gas chromatography indicated that the 1-t-butylazo-1-isocyanatocyclohexane had reacted almost immediately. The reaction mixture was poured into 300 ml water and the product extracted with 100 ml pentane. The pentane extract was separated, washed with water, 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave 11.0 grams (81.5% crude yield) of a yellow liquid. The product had a strong carbonyl band at 1725 cm-1 and a sharp NH band at 3400 cm-1 in its infrared spectrum and the isocyanate band at 2225 cm-1 was absent.

Workup

  1. customcame back to 25° C.
  2. additionAfter the addition
  3. customhad reacted almost immediately
  4. extractionthe product extracted with 100 ml pentane
  5. extractionThe pentane extract
  6. customwas separated
  7. washwashed with water, 10% NaHCO3 solution
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customthe pentane evaporated under reduced pressure
  11. customto leave 11.0 grams (81.5% crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-c262462fdf5c4107b2260b5cf25fbbb7
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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