O-Phenylenediamine → HCID 17863286, compound

HRID 1671842Notes

Reaction equation

HRID 1671842 reaction equation
O.O.O.O.O.O.O.O.O=[C:10]1[C:15](=O)[C:14](=O)[C:13](=O)[C:12](=O)[C:11]1=O.[C:21]1([NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:27]>C(O)(=O)C.C(O)C.C(Cl)(Cl)Cl>[CH:10]1[C:15]2[C:14](=[N:27][C:22]3[C:23]4[C:24]([C:25]5[C:26]([C:21]=3[N:28]=2)=[N:28][C:21]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:27]=5)=[N:28][C:21]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:27]=4)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 2723849HCID 2723849, compound

Product 1

HCID 17863286HCID 17863286, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
140 °C

Procedure

The title compound was synthesized according to a modified literature procedure.30 Hexaketocyclohexane octahydrate (10.0 g, 32.0 mmol) and 1,2-phenylenediamine SM17 (10.4 g, 96.0 mmol) were refluxed in 500 ml of glacial acetic acid:ethanol (1:1) at 140° C. for 24 hours. The reaction mixture was then filtered and washed with ca. 200 ml of hot glacial acid. The solid was then refluxed with 200 ml of 30% nitric acid for 3 hours at 140° C. The yellow solid (12.6 g) was filtered and dried under vacuum. An amount 2.0 g was sublimed at high vacuum (3.2×10−6 torr and t=350° C.) to yield 0.77 g (estimated extrapolated yield=40%) of yellow solid. The yield could be increased with prolonged sublimation time. This compound is slightly soluble in CHCl3. 1H NMR (CDCl3, 300 MHz) δ 8.73-8.69 (dd, J=6.6 Hz; J2=3.6 Hz, 6H), 8.08-8.043 (m, 6H). 13C NMR (CDCl3, 75 MHz), 143.57, 132.30, 130.65, 119.05, 98.58. Anal. Calcd. for C24H12N6: C, 74.99; H, 3.15; N, 21.86. Found: C, 74.76; H, 3.11; N, 21.66.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washwashed with ca. 200 ml of hot glacial acid
  3. filtrationThe yellow solid (12.6 g) was filtered
  4. customdried under vacuum
  5. customwas sublimed at high vacuum (3.2×10−6 torr and t=350° C.)
  6. customto yield 0.77 g (estimated extrapolated yield=40%) of yellow solid
  7. customThe yield could
  8. temperaturebe increased with prolonged sublimation time

Sources & evidence

ORD record
ord-061862a715344fc0b7d4c1ada357e569
Source dataset
uspto-grants-2011_08
Patent number
US07994423B2

Reaction notes

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