Methanol → HCID 21387249, compound

HRID 1834337Notes

Reaction equation

HRID 1834337 reaction equation
[CH3:1][OH:2].[H-].[Na+].[CH:5]([N:9]=[N:10][C:11]([N:17]=[C:18]=[O:19])([CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:12])([CH2:7][CH3:8])[CH3:6]>O>[CH:5]([N:9]=[N:10][C:11]([NH:17][C:18]([O:2][CH3:1])=[O:19])([CH2:13][CH:14]([CH3:15])[CH3:16])[CH3:12])([CH2:7][CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 21387234HCID 21387234, compound

Product 1

HCID 21387249HCID 21387249, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 25 ml of stirred methanol in a 125 ml erlenmeyer flask was slowly added 1.2 grams (0.028 moles) of 57% sodium hydride. The solution was cooled to 25° C in a cold water bath and 5.9 grams (.028 moles) of 2-sec.-butylazo-2-isocyanato-4-methylpentane (from Example XVII) was added dropwise over 5 minutes. The reaction was stirred an additional hour at room temperature, poured into 200 ml water, the product extracted with 100 ml pentane, washed with 100 ml saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure on a rotating evaporator. The product was a yellow liquid and weighed 3.9 grams (57.3% crude yield). The infrared spectrum was in agreement with the structure of 2-sec-butylazo-2-(methoxycarbonylamino)-4-methylpentane (strong carbonyl band at 1740 cm-1, sharp NH at 3375 cm-1 and no isocyanate band at 2125-2225 cm-1).

Workup

  1. extractionthe product extracted with 100 ml pentane
  2. washwashed with 100 ml saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-6cf2d109da1f454f898a42e3ca6d7429
Source dataset
uspto-grants-1978_01
Patent number
US04069377

Reaction notes

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