N-isobutylidene-3-phenoxybenzylamine → 3-Phenoxybenzylidene-isobutylamine

HRID 224269Notes

Reaction equation

HRID 224269 reaction equation
[CH:1](=[N:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)[CH:2]([CH3:4])[CH3:3]>CS(C)=O>[O:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH:6]=[N:5][CH2:1][CH:2]([CH3:3])[CH3:4])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 23332476N-isobutylidene-3-phenoxybenzylamine

Product 1

HCID 233324743-Phenoxybenzylidene-isobutylamineYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

51 g (0.202 mol) of N-isobutylidene-(3-phenoxybenzylamine) is dissolved in 45 ml of dimethyl sulfoxide, and at room temperature (20°-25° C.) is added all at once, with stirring, 2 g (0.0179 mol) of potassium-tert-butylate. The temperature of the reaction solution rises during this addition to 25°-30° C. The solution is stirred for a further hour at room temperature, and is then extracted three times with 50 ml of water each time. The residue is taken up in 30 ml of diethyl ether, dried with magnesium sulfate, and distilled to obtain 48.5 g (0.192 mol) of 3-phenoxybenzylidene-isobutylamine, corresponding to a yield of 95% of theory; b.p. 83° C./4 Pa; nD20 =1.5677.

Workup

  1. additionat room temperature (20°-25° C.) is added all at once,
  2. additionThe temperature of the reaction solution rises during this addition to 25°-30° C
  3. stirringThe solution is stirred for a further hour at room temperature
  4. extractionis then extracted three times with 50 ml of water each time
  5. dry with materialdried with magnesium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-bc88634d1d5d44a0888471f6fa72b2d6
Source dataset
uspto-grants-1980_11
Patent number
US04231962

Reaction notes

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