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

HRID 1627405Notes

Reaction equation

HRID 1627405 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-17b9ad85e020457b8821ae4c3dd8a301
Source dataset
uspto-grants-2014_07
Patent number
US08785589B1

Reaction notes

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