Phthalic Anhydride → HCID 22628889, compound

HRID 277342Notes

Reaction equation

HRID 277342 reaction equation
[NH2:1][C:2]1[CH:68]=[CH:67][C:5]([CH2:6][CH:7]2[C:30](=[O:31])[N:29]([CH3:32])[CH:28]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:27](=[O:37])[O:26][CH:25]([CH3:38])[CH2:24][N:23]([CH3:39])[CH:22]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:21](=[O:44])[O:20][CH:19]([CH2:45][C:46]3[CH:51]=[CH:50][C:49]([NH2:52])=[CH:48][CH:47]=3)[C:18](=[O:53])[N:17]([CH3:54])[CH:16]([CH2:55][CH:56]([CH3:58])[CH3:57])[C:15](=[O:59])[O:14][CH:13]([CH3:60])[CH2:12][N:11]([CH3:61])[CH:10]([CH2:62][CH:63]([CH3:65])[CH3:64])[C:9](=[O:66])[O:8]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:52]([C:49]2[CH:50]=[CH:51][C:46]([CH2:45][CH:19]3[C:18](=[O:53])[N:17]([CH3:54])[CH:16]([CH2:55][CH:56]([CH3:57])[CH3:58])[C:15](=[O:59])[O:14][CH:13]([CH3:60])[CH2:12][N:11]([CH3:61])[CH:10]([CH2:62][CH:63]([CH3:65])[CH3:64])[C:9](=[O:66])[O:8][CH:7]([CH2:6][C:5]4[CH:67]=[CH:68][C:2]([N:1]5[C:69](=[O:79])[C:70]6=[CH:78][CH:77]=[CH:76][CH:75]=[C:71]6[C:72]5=[O:73])=[CH:3][CH:4]=4)[C:30](=[O:31])[N:29]([CH3:32])[CH:28]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:27](=[O:37])[O:26][CH:25]([CH3:38])[CH2:24][N:23]([CH3:39])[CH:22]([CH2:40][CH:41]([CH3:42])[CH3:43])[C:21](=[O:44])[O:20]3)=[CH:47][CH:48]=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 22628891HCID 22628891, compound

Product 1

HCID 22628889HCID 22628889, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

475.6 mg (0.50 mmol) of 8,20-bis-(4-aminobenzyl)-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,9,12,18,21,24-hexaone (for example from Example 4) were initially charged in 1.5 ml of glacial acetic acid and heated under reflux with 162.9 mg (1.1 mmol) of phthalic anhydride for 5 h. The mixture was concentrated, the residue was taken up in tertbutyl methyl ether (MTBE) and washed with sodium bicarbonate solution and saturated sodium chloride solution. The solution was dried with sodium sulfate, reconcentrated and subsequently filtered over a short silica gel column (Ø=3 cm, l=5 cm) using cyclohexane/ethyl acetate 2:1. Evaporation of the filtrate gave 0.55 g of slightly contaminated 8,20-bis-(4-phthalimidobenzyl)-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,9,12,18,21,24-hexaone as a yellow foam.

Workup

  1. temperatureheated
  2. concentrationThe mixture was concentrated
  3. washwashed with sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe solution was dried with sodium sulfate
  5. filtrationreconcentrated and subsequently filtered over a short silica gel column (Ø=3 cm, l=5 cm)
  6. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-688001a3d25841e4aacae7e32f62516f
Source dataset
uspto-grants-2002_03
Patent number
US06355615B1

Reaction notes

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