Methanol → HCID 53787608, compound

HRID 436766Notes

Reaction equation

HRID 436766 reaction equation
[CH3:1][OH:2].[H-].[Na+].[N:5]([C:14]([N:18]=[C:19]=[O:20])([CH2:16][CH3:17])[CH3:15])=[N:6][C:7]([N:11]=[C:12]=[O:13])([CH2:9][CH3:10])[CH3:8].[N-]=[C:22]=[O:23]>O>[N:5]([C:14]([NH:18][C:19]([O:23][CH3:22])=[O:20])([CH2:16][CH3:17])[CH3:15])=[N:6][C:7]([NH:11][C:12]([O:2][CH3:1])=[O:13])([CH2:9][CH3:10])[CH3:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 105034IsocyanateHCID 53785527HCID 53785527, compound

Product 1

HCID 53787608HCID 53787608, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of methanol 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 down to 30° C., 5.6 grams (0.025 moles) of 2,2'-azobis(2-isocyanatobutane) was added dropwise over 2 minutes from an eyedropper. The reaction mixture exothermed to 45° C. over this period. The reaction mixture was stirred an additional 11/2 hours, poured into 200 ml water and the product extracted with a solution of 75 ml of pentane and 40 ml methylene chloride. The organic layer was separated, washed twice with water, once with 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the solvent evaporated under reduced pressure to leave 2.0 grams (28% crude yield) of an orange liquid. The product had a strong carbonyl band at 1700 cm-1 and a sharp NH band at 3340 cm-1 and there is no isocyanate band at 2200 cm-1.

Workup

  1. customcame back down to 30° C.
  2. waitThe reaction mixture exothermed to 45° C. over this period
  3. extractionthe product extracted with a solution of 75 ml of pentane and 40 ml methylene chloride
  4. customThe organic layer was separated
  5. washwashed twice with water, once with 10% NaHCO3 solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customto leave 2.0 grams (28% crude yield) of an orange liquid

Sources & evidence

ORD record
ord-fdf6d54fed24487180ad0e9079c5c913
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

Loading…