Boric Acid → HCID 59297261, compound

HRID 2234743Notes

Reaction equation

HRID 2234743 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:24]([O:25][CH3:26])=[CH:23][C:22]2[C:21]3[C:16](=[CH:17][C:18]([C:27]([NH:29][C:30]4[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:31]=4[OH:37])=O)=[CH:19][CH:20]=3)[C:15]([CH2:41][CH2:42][CH3:43])([CH2:38][CH2:39][CH3:40])[C:14]=2[CH:13]=1)=[O:11].B(O)(O)O>O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]2[O:11][C:10]([C:12]3[C:24]([O:25][CH3:26])=[CH:23][C:22]4[C:21]5[C:16](=[CH:17][C:18]([C:27]6[O:37][C:31]7[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:30]=7[N:29]=6)=[CH:19][CH:20]=5)[C:15]([CH2:41][CH2:42][CH3:43])([CH2:38][CH2:39][CH3:40])[C:14]=4[CH:13]=3)=[N:9][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 7628Boric AcidHCID 59297268HCID 59297268, compound

Product 1

HCID 59297261HCID 59297261, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture N,N′-bis(2-hydroxy-5-methylphenyl)-9,9-dipropyl-3-methoxyfluorene-2,7-dicarboxamide (76.7 g, 0.133 mol), powdered boric acid (1.8 g) and (750 mL) stirred under argon was slowly heated to reflux allowing water to be distilled. After cooling overnight the resulting mixture was further distilled to remove diethylene glycol dibutyl ether (600 mL). The residual mixture was added to methanol (500 mL) causing precipitation of crude product. The mixture was diluted with water (100 mL) and cooled to −20° C. for 18 h. The mixture was filtered and the solid washed with methanol to afford crude product (51.4 g; m. pt. 205-230° C.). Purification by soxhlet extraction with hexane yielded 2,7-Bis(5-methylbenzoxazol-2-yl)-9,9-dipropyl-3-methoxyfluorene (34.6 g; yield 48%).

Workup

  1. temperaturewas slowly heated
  2. temperatureto reflux
  3. distillationto be distilled
  4. temperatureAfter cooling overnight the resulting mixture
  5. distillationwas further distilled
  6. customto remove diethylene glycol dibutyl ether (600 mL)
  7. additionThe residual mixture was added to methanol (500 mL)
  8. customprecipitation of crude product
  9. additionThe mixture was diluted with water (100 mL)
  10. filtrationThe mixture was filtered
  11. washthe solid washed with methanol
  12. customto afford crude product (51.4 g; m. pt. 205-230° C.)
  13. customPurification
  14. extractionby soxhlet extraction with hexane

Sources & evidence

ORD record
ord-6712bf1831b84593ac8cc47a4e7efda0
Source dataset
uspto-grants-2010_05
Patent number
US07713452B2

Reaction notes

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