Methanol → HCID 54416519, compound

HRID 436778Notes

Reaction equation

HRID 436778 reaction equation
[OH-:1].[Na+].[N:3]([C:14]1([N:20]=[C:21]=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[N:4][C:5]1([N:11]=[C:12]=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[N-]=[C:24]=[O:25].[CH3:26]O>CCCCC.O>[N:3]([C:14]1([NH:20][C:21]([O:25][CH3:24])=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[N:4][C:5]1([NH:11][C:12]([O:1][CH3:26])=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 105034IsocyanateHCID 53902663HCID 53902663, compound

Product 1

HCID 54416519HCID 54416519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8003PentaneSolvent

Procedure

To a stirred solution of 4.77 grams (.0596 moles) of 50% sodium hydroxide in 30 mls of methanol in a 125 ml erlenmeyer flask cooled in an ice bath, was added a solution of 8.1 grams (.0298 moles) of 1,1'-azobis (1-isocyanatocyclohexane) (from Example XCI) in 25 ml of pentane. After the addition was complete, the reaction was stirred an additional 90 minutes at 0°-5° C., diluted with 150 ml cold water and the pentane layer separated. The pentane solution was washed with water, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave 3.3 grams (33% crude yield) of a yellow liquid. The infrared spectrum of the product contained a strong sharp carbonyl band at 1730 cm-1 and a sharp NH band at 3330 cm-1. The isocyanate band of the starting material at 2225 cm-1 was absent.

Workup

  1. additionAfter the addition
  2. customthe pentane layer separated
  3. washThe pentane solution was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe pentane evaporated under reduced pressure
  7. customto leave 3.3 grams (33% crude yield) of a yellow liquid

Sources & evidence

ORD record
ord-fddf7bbd52f7480aa0032c0521918e9e
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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