Methanol → HCID 21431238, compound

HRID 436767Notes

Reaction equation

HRID 436767 reaction equation
CO.[H-].[Na+].[C:5]([N:9]=[N:10][C:11]1([N:17]=[C:18]=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:8])([CH3:7])[CH3:6].[N-]=[C:21]=[O:22]>O>[C:5]([N:9]=[N:10][C:11]1([NH:17][C:18]([O:22][CH3:21])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 105034IsocyanateHCID 214311721-t-Butylazo-1-isocyanatocyclohexane2×

Product 1

HCID 21431238HCID 21431238, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of methanol in a 100 ml 3 neck round bottom flask equipped with a thermometer and 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-1-isocyanatocyclohexane was added dropwise over 5 minutes. There was a 2° C. rise in temperature during the addition. 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 methylene chloride. The methylene chloride extract was separated, washed with water, 100 ml 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the methylene chloride evaporated under reduced pressure to leave 11.0 grams (91% crude yield) of a yellow liquid. The product had a strong carbonyl band at 1730 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. customwas a 2° C.
  3. additionduring the addition
  4. additionAfter the addition
  5. customhad reacted almost immediately
  6. extractionthe product extracted with 100 ml methylene chloride
  7. extractionThe methylene chloride extract
  8. customwas separated
  9. washwashed with water, 100 ml 10% NaHCO3 solution
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. customthe methylene chloride evaporated under reduced pressure
  13. customto leave 11.0 grams (91% crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-ac2aff191cf647f385c064b4e7fe24c4
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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