1-Butanol → HCID 68719478, compound

HRID 2164861Notes

Reaction equation

HRID 2164861 reaction equation
NC1C=CC(CC2C=C(CC3C=C[C:18]([NH2:21])=CC=3)C=CC=2N)=CC=1.[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1.[CH2:38]=[O:39].C([OH:44])CCC>>[OH:39][C:38]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[O:30][NH:21][C:18]=1[OH:44]

Participants

6

Reactant 5

HCID 2631-ButanolHCID 712FormaldehydeHCID 996PhenolHCID 1140TolueneHCID 331822,4-Bis(4-aminobenzyl)aniline

Product 1

HCID 68719478HCID 68719478, compound

Conditions

Temperature
60 °C

Procedure

To a reactor are charged 110 parts of 2,4-bis(p-aminobenzyl)aniline (a technical grade by-product sold by E. I. duPont de Nemours & Co.), 94 parts of phenol, 160 parts of toluene and 40 parts of n-butanol. The reactor is inerted with nitrogen and heated to 60° C. with stirring to form a uniform solution. At 60° C. 128 parts of 50% formalin are added rapidly allowing the temperature to rise to atmospheric reflux (reflux temperature ~91° C.). The batch is refluxed for 3 hours during which time the reflux condensate is returned to the reactor. After 3 hours the reflux condensate is separated into an aqueous phase and organic phase in an oil water separator. The organic phase of the condensate is returned to the reactor and the aqueous phase is removed from the reaction mixture. The reaction temperature is allowed to go to 110° C. at atmospheric pressure. The solution of product is cooled and filtered. The product has a % closed dihydrobenzoxazine ring of 87% and a calculated equivalent weight of 263. The reddish product solution has a solids content of 59%.

Workup

  1. customto form a uniform solution
  2. customAt 60° C
  3. temperatureto atmospheric reflux
  4. temperature(reflux temperature ~91° C.)
  5. temperatureThe batch is refluxed for 3 hours during which time the reflux condensate
  6. customAfter 3 hours the reflux condensate is separated into an aqueous phase and organic phase in an oil water separator
  7. customthe aqueous phase is removed from the reaction mixture
  8. customto go to 110° C. at atmospheric pressure
  9. temperatureThe solution of product is cooled
  10. filtrationfiltered
  11. customclosed dihydrobenzoxazine ring of 87%

Sources & evidence

ORD record
ord-6cbe8475f7814a08829827b08d453782
Source dataset
uspto-grants-1985_03
Patent number
US04507428

Reaction notes

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