Triethylamine → HCID 86696062, compound

HRID 628204Notes

Reaction equation

HRID 628204 reaction equation
[C:1]1([C:7]2[O:12][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][C:16]([C:18](Cl)=[O:19])=[CH:17][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([NH2:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(N(CC)CC)C>O1CCCC1>[CH2:21]([NH:33][C:18]([C:16]1[CH:15]=[CH:14][C:10]2[C:11](=[O:13])[O:12][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][C:9]=2[CH:17]=1)=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13583DodecylamineHCID 11737727HCID 11737727, compound

Product 1

HCID 86696062HCID 86696062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The synthesis started out from 2-phenyl-7-chlorocarbonyl-4H-3,1-benzoxazin-4-one, whose synthesis is descried in L. Jakisch et al., Journal of Polymer Science: Part A: Polymer Chemistry 2003; 41(5): 655-667 (there compound 10a). 2.855 g (10 mmol) of this substance was suspended in 100 ml of dry tetrahydrofuran at 0° C. in a 250 ml three-necked flask provided with magnetic stirrer, reflux condenser and drying tube. A mixture of 1.854 g (10 mmol) of n-dodecylamine, 1.012 g (10 mmol) of triethylamine and 20 ml of dry tetrahydrofuran was then slowly added dropwise at from 0 to 5° C. The reaction mixture was subsequently stirred at room temperature for 2 hours, and the resultant precipitate of triethylammonium chloride was then filtered off with suction and the filtrate was evaporated on a rotary evaporator. The solid residue was washed with water and dried at 60° C. under reduced pressure. Recrystallization from ethanol gave 2.85 g of product.

Workup

  1. customprovided with magnetic stirrer
  2. temperaturereflux condenser
  3. customdrying tube
  4. additionwas then slowly added dropwise at from 0 to 5° C
  5. filtrationthe resultant precipitate of triethylammonium chloride was then filtered off with suction
  6. customthe filtrate was evaporated on a rotary evaporator
  7. washThe solid residue was washed with water
  8. customdried at 60° C. under reduced pressure
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-aee8ffbec1994e5886dfcf18e8686c0b
Source dataset
uspto-grants-2016_04
Patent number
US09312043B2

Reaction notes

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