Formaldehyde → Dihydrobenzoxazine

HRID 1928517

Reaction equation

HRID 1928517 reaction equation
[NH2:1][CH2:2][C:3]12CCCC1C1CC2(CN)CC1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C=O>C(Cl)(Cl)Cl>[O:21]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:3][CH2:2][NH:1]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 996Phenol2×HCID 53737527Bis(aminomethyl)tricyclo[5,2,1,02,6]decane

Product 1

HCID 21887592Dihydrobenzoxazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
60 °C

Procedure

One mole of 3(4),8(9),-bis(aminomethyl)tricyclo[5,2,1,02,6]decane as saturated alicyclic hydrocarbon diamine compound having a condensed ring structure, two moles of phenol as the phenol compound represented by Formula (1), as well as, 4 moles of paraformaldehyde as aldehyde compound and 1500 g of chloroform were mixed. This mixture was heated to 60° C. under stirring, and the reaction was carried out for 6 hours since chloroform started circulating. After the end of the reaction, the reaction mixture was washed with an aqueous solution of 1 N sodium hydroxide, and then rinsed with ion exchanged water. Then, after the chloroform phase was dried with anhydrous sodium sulfate, chloroform was evaporated with a rotary evaporator to obtain a bifunctional dihydro benzoxazine compound in which R14 of Formula (2) is the amino residue of 3(4),8(9),-bis(aminomethyl)tricyclo[5,2,1,02,6]decane.

Workup

  1. customAfter the end of the reaction
  2. washthe reaction mixture was washed with an aqueous solution of 1 N sodium hydroxide
  3. washrinsed with ion
  4. dry with materialThen, after the chloroform phase was dried with anhydrous sodium sulfate, chloroform
  5. customwas evaporated with a rotary evaporator

Sources & evidence

ORD record
ord-0c98b5027cee4fd08448c6f83a4a0314
Source dataset
uspto-grants-2012_05
Patent number
US08183368B2

Linked notes

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