Hydrazine hydrate (1:1) → 4,5-Bis(dodecyloxy)benzene-1,2-diamine

HRID 1671843Notes

Reaction equation

HRID 1671843 reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[C:17]([N+:23]([O-])=O)=[CH:16][C:15]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.NN>[Pd].C(O)C>[CH2:1]([O:13][C:14]1[CH:19]=[C:18]([NH2:20])[C:17]([NH2:23])=[CH:16][C:15]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10768708HCID 10768708, compound

Product 1

HCID 153304314,5-Bis(dodecyloxy)benzene-1,2-diamineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

This compound was synthesized according to a literature procedure.24 In a Schlenk tube, 1,2-Bis-dodecyloxy-4,5-dinitro benzene BK2—13 (2.36 g, 4.39 mmol), hydrazine monohydrate (8.25 ml, 48.5 mmol), 131 mg of Pd/C, and 65 ml of absolute ethanol were placed. The reaction mixture was refluxed under argon for 22 hours. Hot filtration under argon was then performed. Upon cooling, a white solid formed. The solid was washed with O2-free methanol and was dried overnight under nitrogen to yield 1.57 g (75%) of white solid. 1H (300 MHz, CDCl3) δ 6.353 (s, 2H), 3.880-3.835 (t, J=6.6 Hz, 4H), 3.062 (br s, 4H, NH2), 1.767-1.673 (pentet, J=7.2 Hz, 4H), 1.43-1.36 (m, 4H), 1.358-1.080 (m, 32H), 0.878-0.833 (t, J=7.2 Hz, 6H).13C (CDCl3, 75 MHz) δ 143.20, 128.20, 106.69, 70.67, 32.00, 29.78, 29.73, 29.67, 29.55, 29.45, 26.17, 22.78, 14.22 ppm. HRMS-E1 (m/z): [M]+ calcd. for C30H56N2O2, 476.43418. found 476.43449.

Workup

  1. customThis compound was synthesized
  2. customaccording to a literature procedure.24 In a Schlenk tube
  3. temperatureThe reaction mixture was refluxed under argon for 22 hours
  4. filtrationHot filtration under argon
  5. temperatureUpon cooling
  6. customa white solid formed
  7. washThe solid was washed with O2-free methanol
  8. customwas dried overnight under nitrogen

Sources & evidence

ORD record
ord-42a1412682fa40aa9451b75777948265
Source dataset
uspto-grants-2011_08
Patent number
US07994423B2

Reaction notes

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