Water → HCID 57782428, compound

HRID 414871Notes

Reaction equation

HRID 414871 reaction equation
FC(F)(F)C(O)=O.C1N2CN3CN(C2)CN1C3.[CH2:18]([C:30]1[C:35]([CH3:36])=[C:34]([CH2:37][OH:38])[C:33]([OH:39])=[C:32]([CH3:40])[CH:31]=1)[C:19]1[C:24]([CH3:25])=[C:23]([CH2:26][OH:27])[C:22]([OH:28])=[C:21]([CH3:29])[CH:20]=1.O>C1(C)C=CC=CC=1.C(C(C)=O)C(C)C>[CH2:18]([C:19]1[C:24]([CH3:25])=[C:23]([CH:26]=[O:27])[C:22]([OH:28])=[C:21]([CH3:29])[CH:20]=1)[C:30]1[C:35]([CH3:36])=[C:34]([CH:37]=[O:38])[C:33]([OH:39])=[C:32]([CH3:40])[CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 10892452HCID 10892452, compound

Product 1

HCID 57782428HCID 57782428, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

171.0 g (1.5 mol) of trifluoroacetic acid was put in a four-way flask with a capacity of 1 liter and the reaction container was substituted by nitrogen, after which 47.3 g (0.34 mol) of hexamethylene tetramine was added at a temperature of approx. 25° C., and then 47.4 g (0.15 mol) of 4,4′-methylene bis(2,5-dimethyl-6-hydroxymethylphenol) was added under agitation over 2.5 hours at a temperature of 50° C. to cause reaction. After the entire amount of the material had been added, the temperature was raised to 80° C., and then the mixture was further agitated for 20 hours as a post-reaction. Next, 150.0 g of water was added to the mixture liquid obtained from the reaction to implement hydrolysis reaction for 1 hour at a temperature of 70° C. (crystal precipitated during this reaction). 245.7 g of 16% aqueous sodium hydroxide solution was added to neutralize the obtained mixture liquid, which was then kept at a temperature of 80° C. for 1 hour. Thereafter, the mixture was cooled and precipitated crystal was filtered out to obtain 72.3 g of coarse crystal. Next, the obtained coarse crystal was put in a four-way flask with a capacity of 1 liter, and then 70.0 g of methyl isobutyl ketone and 50.0 g of toluene were added and the mixture was kept at a temperature of 80° C. for 1 hour (the solution was in a slurry state), after which the mixture was cooled and precipitated crystal was filtered out and dried to obtain 45.3 g of yellow powder having a purity of 94.6% based on HPLC.

Workup

  1. customreaction
  2. additionAfter the entire amount of the material had been added
  3. customobtained from the reaction
  4. customhydrolysis reaction for 1 hour at a temperature of 70° C. (crystal
  5. customprecipitated during this reaction)
  6. addition245.7 g of 16% aqueous sodium hydroxide solution was added
  7. waitwas then kept at a temperature of 80° C. for 1 hour
  8. temperatureThereafter, the mixture was cooled
  9. customprecipitated crystal
  10. filtrationwas filtered out
  11. customto obtain 72.3 g of coarse crystal
  12. customNext, the obtained coarse crystal
  13. waitthe mixture was kept at a temperature of 80° C. for 1 hour
  14. temperaturewas cooled
  15. customprecipitated crystal
  16. filtrationwas filtered out
  17. customdried

Sources & evidence

ORD record
ord-dfb5465ad38646ad942b1e3553e7fc8c
Source dataset
uspto-grants-2012_01
Patent number
USRE043067E1

Reaction notes

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