Hydrochloric Acid → HCID 86762549, compound

HRID 1773294Notes

Reaction equation

HRID 1773294 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:77]=[CH:76][C:16]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([C:51]4[CH:56]=[CH:55][C:54]([O:57][C:58]5[CH:63]=[CH:62][C:61]([N:64]=[N:65][C:66]6[CH:71]=[CH:70][C:69]([NH:72]C(=O)C)=[CH:68][CH:67]=6)=[CH:60][CH:59]=5)=[CH:53][CH:52]=4)([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]5[CH:38]=[CH:37][C:36]([N:39]=[N:40][C:41]6[CH:46]=[CH:45][C:44]([NH:47]C(=O)C)=[CH:43][CH:42]=6)=[CH:35][CH:34]=5)=[CH:28][CH:27]=4)[CH3:25])=[CH:20][CH:19]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=O)C.Cl.C(O)C>O>[NH2:47][C:44]1[CH:43]=[CH:42][C:41]([N:40]=[N:39][C:36]2[CH:37]=[CH:38][C:33]([O:32][C:29]3[CH:30]=[CH:31][C:26]([C:24]([C:21]4[CH:22]=[CH:23][C:18]([O:17][C:16]5[CH:76]=[CH:77][C:13]([N:12]=[N:11][C:8]6[CH:9]=[CH:10][C:5]([NH2:4])=[CH:6][CH:7]=6)=[CH:14][CH:15]=5)=[CH:19][CH:20]=4)([C:51]4[CH:52]=[CH:53][C:54]([O:57][C:58]5[CH:63]=[CH:62][C:61]([N:64]=[N:65][C:66]6[CH:71]=[CH:70][C:69]([NH2:72])=[CH:68][CH:67]=6)=[CH:60][CH:59]=5)=[CH:55][CH:56]=4)[CH3:25])=[CH:27][CH:28]=3)=[CH:34][CH:35]=2)=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86762548HCID 86762548, compound

Product 1

HCID 86762549HCID 86762549, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 100 mL round-bottomed flask with a stir-bar and a condenser, 1,1,1-tris[4-(4-(4-acetamidophenyldiazenyl)phenoxy)phenyl]ethane (Example 4; 0.50 g, 0.49 mmol), 6 M HCl (20 mL) and 95% ethanol (20 mL) were charged and heated to 80° C. The mixture was stirred at 80° C. for 3 days. After the mixture was allowed to cool to room temperature, water (60 mL) added. The resulting red solid was collected by filtration and washed with dilute sodium bicarbonate solution, followed by deionized water (300 mL). After being air dried, the crude product was purified by column chromatography (silica gel, ethyl acetate as eluent). The solvent was removed by a rotary evaporator to afford 0.23 g (52.5%) of orange red solid, mp >300° C. MS (m/e): 892 (M+). Anal. Calcd. for C56H45N9O3: C, 75.40%; H, 5.08%; N, 14.13%. Found: C, 75.44%; H, 5.08%; N, 13.98%. 1H-NMR (d6-DMSO, δ in ppm): 2.12 (s, 3H, CCH3), 6.03 (s, 6H, NH2), 6.67-6.70 (d, 6H, J=8.7 Hz), 6.99-7.02 (d, 6H, J=8.7 Hz), 7.09-7.13 (m, 12H), 7.62-7.66 (d, 6H, J=8.7 Hz), 7.75-7.78 (d, 6H, J=8.7 Hz). 13C-NMR (d6-DMSO, δ in ppm): 30.34, 51.91, 113.41, 118.44, 118.69, 123.52, 124.96, 129.93, 142.92, 144.25, 148.41, 152.56, 154.21, 157.75.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting red solid was collected by filtration
  3. washwashed with dilute sodium bicarbonate solution
  4. customdried
  5. customthe crude product was purified by column chromatography (silica gel, ethyl acetate as eluent)
  6. customThe solvent was removed by a rotary evaporator

Sources & evidence

ORD record
ord-ef050cb1d5ca4e439e79729c3ea2fb6c
Source dataset
uspto-grants-2016_02
Patent number
US09255065B1

Reaction notes

Loading…