Acetic Acid → HCID 86762548, compound

HRID 1773293Notes

Reaction equation

HRID 1773293 reaction equation
[NH2:1][C:2]1[CH:44]=[CH:43][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=4)=[CH:31][CH:30]=3)([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[CH3:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N:45]([C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54](=[O:56])[CH3:55])=[CH:49][CH:48]=1)=O.[C:57]([OH:60])(=O)[CH3:58]>C(O)C>[C:54]([NH:53][C:50]1[CH:51]=[CH:52][C:47]([N:45]=[N:42][C:39]2[CH:40]=[CH:41][C:36]([O:35][C:32]3[CH:33]=[CH:34][C:29]([C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:21][C:22]5[CH:27]=[CH:26][C:25]([N:28]=[N:45][C:47]6[CH:52]=[CH:51][C:50]([NH:53][C:57](=[O:60])[CH3:58])=[CH:49][CH:48]=6)=[CH:24][CH:23]=5)=[CH:19][CH:20]=4)([C:10]4[CH:9]=[CH:8][C:7]([O:6][C:5]5[CH:4]=[CH:3][C:2]([N:1]=[N:45][C:47]6[CH:48]=[CH:49][C:50]([NH:53][C:54](=[O:56])[CH3:55])=[CH:51][CH:52]=6)=[CH:44][CH:43]=5)=[CH:12][CH:11]=4)[CH3:14])=[CH:30][CH:31]=3)=[CH:37][CH:38]=2)=[CH:48][CH:49]=1)(=[O:56])[CH3:55]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 19001763N-(4-Nitrosophenyl)acetamideHCID 66650022HCID 66650022, compound

Product 1

HCID 86762548HCID 86762548, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1,1-Tris(4-(4-aminophenoxy)phenyl)ethane (Example 2; 0.580 g, 1.00 mmol), N-(4-nitrosophenyl)acetamide (Example 3; 0.985 g, 6 mmol) and acetic acid (20 mL) were charged into a 150 mL round-bottomed flask equipped with a magnetic stir bar. The mixture was stirred at room temperature for 48 hours. The mixture was at first turned into a greenish solution, and then yellow particles started to precipitate out of the solution. The mixture was diluted by deionized water (100 mL). Solids were collected and washed with water (500 mL), followed by ethanol (200 mL) to remove most of the unreacted nitroso reagent. The solid was then extracted by hot acetone (100 mL) four times. The acetone extract was concentrated on a rotary evaporator to give yellow solids as raw product. The raw product was slurried in hot ethanol (50 mL) and filtered twice after cooling to room temperature in between to give 0.62 g (61%) of yellow solids, mp 220° C. (dec.). 1H-NMR (d6-DMSO, δ in ppm): 2.09 (s, 9H, COCH3), 2.15 (s, 3H, CCH3) 7.03-7.15 (m, 18H), 7.79-7.87 (m, 18H) 10.28 (s, 3H, NHCO). 13C-NMR (d6-DMSO, δ in ppm): 24.16, 30.28, 51.00, 118.50, 118.86, 119.18, 123.42, 124.35, 129.99, 142.09, 144.50, 147.38, 147.77, 153.78, 159.07, 168.06.

Workup

  1. customequipped with a magnetic stir bar
  2. customto precipitate out of the solution
  3. additionThe mixture was diluted by deionized water (100 mL)
  4. customSolids were collected
  5. washwashed with water (500 mL)
  6. customto remove most of the unreacted nitroso reagent
  7. extractionThe solid was then extracted by hot acetone (100 mL) four times
  8. extractionThe acetone extract
  9. concentrationwas concentrated on a rotary evaporator
  10. customto give yellow solids as raw product
  11. filtrationfiltered twice
  12. temperatureafter cooling to room temperature in between

Sources & evidence

ORD record
ord-fc23dfa04cc94671a130790faed693ee
Source dataset
uspto-grants-2016_02
Patent number
US09255065B1

Reaction notes

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