Methanol → HCID 21431239, compound

HRID 436773Notes

Reaction equation

HRID 436773 reaction equation
CO.[H-].[Na+].[C:5]([N:9]=[N:10][C:11]([N:14]=[C:15]=[O:16])([CH3:13])[CH3:12])([CH3:8])([CH3:7])[CH3:6].[N-]=[C:18]=[O:19]>O>[C:5]([N:9]=[N:10][C:11]([NH:14][C:15]([O:19][CH3:18])=[O:16])([CH3:13])[CH3:12])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 105034IsocyanateHCID 373155HCID 373155, compound

Product 1

HCID 21431239HCID 21431239, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 50 ml of methanol in a 125 ml erlenmeyer flask stirred with a magnetic stirrer was slowly added 3.1 grams (0.075 moles) of 57% sodium hydride. The reaction mixture was cooled back to 25° C. and 12.7 grams (0.075 moles) of 2-t-butylazo-2-isocyanatopropane (from Example XIV) was added dropwise over 5 minutes. The reaction mixture was stirred for approximately 1 hour, poured into 200 ml water and the product extracted with pentane. The pentane extract was washed with water, 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave 11.8 grams (78% crude yield) of a yellow liquid. The product contained a strong carbonyl band at approximately 1740 cm-1 and a sharp NH band at approximately 3375 cm-1 in its infrared spectrum and there was no isocyanate band at 2225 cm-1.

Workup

  1. extractionthe product extracted with pentane
  2. extractionThe pentane extract
  3. washwas washed with water, 10% NaHCO3 solution
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe pentane evaporated under reduced pressure
  7. customto leave 11.8 grams (78% crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-8944d14c12c849e78659a8f493c30ab8
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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