Phthalic Anhydride → HCID 90290569, compound

HRID 1773295Notes

Reaction equation

HRID 1773295 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[CH:68]=[CH:67][C:13]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([C:45]4[CH:50]=[CH:49][C:48]([O:51][C:52]5[CH:57]=[CH:56][C:55]([N:58]=[N:59][C:60]6[CH:65]=[CH:64][C:63]([NH2:66])=[CH:62][CH:61]=6)=[CH:54][CH:53]=5)=[CH:47][CH:46]=4)([C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][C:33]([N:36]=[N:37][C:38]6[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=6)=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)[CH3:22])=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:69]1(=[O:79])O[C:72](=[O:73])[C:71]2=[CH:75][CH:76]=[CH:77][CH:78]=[C:70]12>C(O)(=O)C>[C:69]1(=[O:79])[N:66]([C:63]2[CH:64]=[CH:65][C:60]([N:59]=[N:58][C:55]3[CH:56]=[CH:57][C:52]([O:51][C:48]4[CH:49]=[CH:50][C:45]([C:21]([C:23]5[CH:24]=[CH:25][C:26]([O:29][C:30]6[CH:35]=[CH:34][C:33]([N:36]=[N:37][C:38]7[CH:43]=[CH:42][C:41]([N:44]8[C:69](=[O:79])[C:70]9=[CH:78][CH:77]=[CH:76][CH:75]=[C:71]9[C:72]8=[O:73])=[CH:40][CH:39]=7)=[CH:32][CH:31]=6)=[CH:27][CH:28]=5)([C:18]5[CH:19]=[CH:20][C:15]([O:14][C:13]6[CH:67]=[CH:68][C:10]([N:9]=[N:8][C:5]7[CH:4]=[CH:3][C:2]([N:1]8[C:72](=[O:73])[C:71]9=[CH:75][CH:76]=[CH:77][CH:78]=[C:70]9[C:69]8=[O:79])=[CH:7][CH:6]=7)=[CH:11][CH:12]=6)=[CH:16][CH:17]=5)[CH3:22])=[CH:46][CH:47]=4)=[CH:53][CH:54]=3)=[CH:61][CH:62]=2)[C:72](=[O:73])[C:71]2=[CH:75][CH:76]=[CH:77][CH:78]=[C:70]12

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 86762549HCID 86762549, compound

Product 1

HCID 90290569HCID 90290569, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a 250 mL three-necked flask equipped with a magnetic stir bar and nitrogen inlet and outlet were placed 1,1,1-tris{4-[4-(4-aminophenyldiazenyl)phenoxy]phenyl}ethane (Example 5; 0.892 g, 1.00 mmol), phthalic anhydride (0,444 g, 3.00 mmol) and acetic acid (20 mL). The mixture was stirred under refluxing for 14 hours and allowed to cool to room temperature. The precipitate was collected by filtration and dried in an oven to afford 0.96 g (75%) of orange powder, mp >300° C. MS (m/e): 1282 (M+). Anal. Calcd. for C80H51N9O9: C, 74.93%; H, 4.01%; N, 9.83%. Found: C, 75.00%; H, 4.11%; N, 9.44%. 1H-NMR (d6-DMSO, δ in ppm): 2.21 (s, 3H, CCH3), 7.08-7.13 (d, 6H, Ar—H), 7.19-7.21 (dd, 12H, Ar—H), 7.67-7.71 (d, 6H, Ar—H), 7.87-8.03 (m, 24H, Ar—H).

Workup

  1. customInto a 250 mL three-necked flask equipped with a magnetic stir bar and nitrogen inlet and outlet
  2. temperatureunder refluxing for 14 hours
  3. filtrationThe precipitate was collected by filtration
  4. customdried in an oven

Sources & evidence

ORD record
ord-5127f37056a84cd791ace99c3355c689
Source dataset
uspto-grants-2016_02
Patent number
US09255065B1

Reaction notes

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