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Potassium Iodide → HCID 16178995, compound

HRID 1488443
Notes
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Reaction equation

HRID 1488443 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[NH:13][C:12]([C:14]([C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([OH:52])[CH:47]=4)=[C:15]4[N:45]=[C:18]([C:19]([C:38]5[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=5)=[C:20]5[NH:37][C:23](=[C:24]([C:30]6[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=6)[C:25]6[CH:26]=[CH:27][C:28]=2[N:29]=6)[CH:22]=[CH:21]5)[CH:17]=[CH:16]4)=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]=1.[C:53](=[O:56])([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:62][CH2:63][CH2:64][N:65]1[C:69](=[O:70])[C:68]2=[CH:71][CH:72]=[CH:73][CH:74]=[C:67]2[C:66]1=[O:75]>CN(C)C=O>[C:53]1(=[O:56])[N:65]([CH2:64][CH2:63][CH2:62][O:52][C:48]2[CH:47]=[C:46]([C:14]3[C:12]4[NH:13][C:9]([C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:62][CH2:63][CH2:64][N:65]6[C:69](=[O:70])[C:68]7=[CH:71][CH:72]=[CH:73][CH:74]=[C:67]7[C:66]6=[O:75])[CH:3]=5)=[C:28]5[N:29]=[C:25]([C:24]([C:30]6[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:62][CH2:63][CH2:64][N:65]7[C:69](=[O:70])[C:68]8=[CH:71][CH:72]=[CH:73][CH:74]=[C:67]8[C:66]7=[O:75])[CH:31]=6)=[C:23]6[NH:37][C:20](=[C:19]([C:38]7[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH2:62][CH2:63][CH2:64][N:65]8[C:69](=[O:70])[C:68]9=[CH:71][CH:72]=[CH:73][CH:74]=[C:67]9[C:66]8=[O:75])[CH:39]=7)[C:18]7[CH:17]=[CH:16][C:15]=3[N:45]=7)[CH:21]=[CH:22]6)[CH:26]=[CH:27]5)=[CH:10][CH:11]=4)[CH:51]=[CH:50][CH:49]=2)[C:66](=[O:75])[C:67]2=[CH:68][CH:71]=[CH:72][CH:73]=[C:74]12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 135462976Tetra(3-hydroxyphenyl)porphyrin

Product 1

HCID 16178995HCID 16178995, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
21 °C

Procedure

7.56 g (11.14 mmol) of 5,10,15,20-tetrakis-(3-hydroxyphenyl)-porphyrin [CARN 22112-79-4] is dissolved in 300 ml of anhydrous N,N-dimethylformamide and mixed with 30.79 g (222.8 mmol) of potassium carbonate and 7.40 g (44.55 mmol) of potassium iodide. 59.72 g (222.8 mmol) of N-(3-bromopropyl)-phthalimide is added to the suspension that is stirred under argon at 21° C. After 24 hours of stirring with exclusion of light, the suspension is filtered, the filtrate is largely concentrated by evaporation in a vacuum, mixed with dichloromethane and shaken out twice with water. The organic phase is dried on anhydrous magnesium sulfate, filtered and concentrated by evaporation, the residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol. The product fractions are concentrated by evaporation, taken up in a little dichloromethane and the title compound is precipitated by the addition of diethyl ether.

Workup

  1. stirringAfter 24 hours of stirring with exclusion of light
  2. filtrationthe suspension is filtered
  3. concentrationthe filtrate is largely concentrated by evaporation in a vacuum
  4. additionmixed with dichloromethane
  5. stirringshaken out twice with water
  6. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customthe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol
  10. concentrationThe product fractions are concentrated by evaporation
  11. customthe title compound is precipitated by the addition of diethyl ether

Sources & evidence

ORD record
ord-8c5d591e9abd4d1187d7067ac7c704d3
Source dataset
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05674467

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes