Benzaldehyde → 2,6,6-Triphenyl-tetrahydro-1,3-oxazine

HRID 596162Notes

Reaction equation

HRID 596162 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][NH2:5].S([O-])([O-])(=O)=O.[Mg+2].[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[C:25]1([CH:24]2[NH:5][CH2:4][CH2:3][C:2]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[O:1]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 20540392HCID 20540392, compound

Product 1

HCID 203266662,6,6-Triphenyl-tetrahydro-1,3-oxazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the stirred mixture of 133.4 g of 3-hydroxy-3,3-diphenylpropylamine, 36 g of anhydrous magnesium sulfate and 250 ml of methylene chloride, the solution of 15.6 g of benzaldehyde in 50 ml of methylene chloride is added. The suspension is stirred for 15 hours at room temperature, heated to the boil and filtered. The residue is washed 3 times with 100 ml of methylene chloride, the combined filtrates evaporated and the residue recrystallized from ethanol, to yield the corresponding cyclic Schiff's base, i.e. the 2,6,6,-triphenyl-tetrahydro-1,3-oxazine melting 163°-165°.

Workup

  1. temperatureheated to the boil
  2. filtrationfiltered
  3. washThe residue is washed 3 times with 100 ml of methylene chloride
  4. customthe combined filtrates evaporated
  5. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-241caae995b0487fb50b3cf5d20520ff
Source dataset
uspto-grants-1977_03
Patent number
US04010166

Reaction notes

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