1,1',1''-(Ethane-1,1,1-triyl)tris[4-(4-nitrophenoxy)benzene] → HCID 66650022, compound

HRID 1773291Notes

Reaction equation

HRID 1773291 reaction equation
[N+:1]([C:4]1[CH:50]=[CH:49][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:33]3[CH:38]=[CH:37][C:36]([O:39][C:40]4[CH:45]=[CH:44][C:43]([N+:46]([O-])=O)=[CH:42][CH:41]=4)=[CH:35][CH:34]=3)([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C1COCC1>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][C:20]2[CH:19]=[CH:18][C:17]([C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][C:7]4[CH:49]=[CH:50][C:4]([NH2:1])=[CH:5][CH:6]=4)=[CH:10][CH:11]=3)([C:33]3[CH:34]=[CH:35][C:36]([O:39][C:40]4[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=4)=[CH:37][CH:38]=3)[CH3:16])=[CH:22][CH:21]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 713539281,1',1''-(Ethane-1,1,1-triyl)tris[4-(4-nitrophenoxy)benzene]

Product 1

HCID 66650022HCID 66650022, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1,1,1-Tris[4-(4-nitrophenoxy)phenyl]ethane (Example 1; 3; 5.0 g, 7.5 mmol), THF (50 mL) and 5% palladium on activated carbon (0.50 g) were added to a hydrogenation bottle. The bottle was secured on a Parr hydrogenation apparatus, flushed three times with hydrogen, and then pressurized to 55 psi. After the mixture had been agitated at room temperature for 24 hours under the hydrogen pressure of 55 psi, it was filtered through Celite. The filter cake was washed with THF, and then the filtrate was evaporated to dryness on a rotary evaporator to afford a 4.25 g (98%) of yellow crystal, which was used without further purification, m.p. 220-221° C. MS (m/e): 579 (M+). Anal. Calcd. for C38H33N3O3: C, 78.73%; H, 5.74%; N, 7.25%. Found: C, 78.17%; H, 5.78%; N, 7.04%. FT-IR (KBr, cm−1): 3441, 3361 (NH2), 3035, 2970, 1617, 1581, 1497, 1384, 1232, 1173, 1117, 1010, 871, 842. 1H-NMR (DMSO-d6, δ in ppm): 2.02 (s, 3H, CH3), 4.99 (s, 6H, NH2), 6.53-6.58 (d, 6H, Ar—H), 6.68-6.74 (m, 12H, Ar—H), 6.88-6.93 (d, 6H, Ar—H).

Workup

  1. customflushed three times with hydrogen
  2. filtrationwas filtered through Celite
  3. washThe filter cake was washed with THF
  4. customthe filtrate was evaporated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-3bef234dd3c94cef8771e21207a0e47d
Source dataset
uspto-grants-2016_02
Patent number
US09255065B1

Reaction notes

Loading…