Hydrochloric Acid → HCID 66672038, compound

HRID 1516658Notes

Reaction equation

HRID 1516658 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[C:24]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:23]=1.[C:37]1(=[O:47])[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39](=[O:46])[NH:38]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[C:33]([C:24]1[CH:23]=[C:22]([C:6]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2][N:38]2[C:39](=[O:46])[C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:37]2=[O:47])[CH:27]=[CH:26][C:25]=1[N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 66672072HCID 66672072, compound

Product 1

HCID 66672038HCID 66672038, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a 50 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer, 1.0 g (1.82 mmol) of ethyl 4′-(3-bromopropyl)-3″-tert-butyl-4″-diethylamino[1,1′;3′,1″]terphenyl-4-carboxylate, 294 mg (2 mmol) of isoindole-1,3-dione and 276 mg of potassium carbonate (2 mmol) are placed in 20 mL of dimethylformamide. The reaction medium is heated at 100° C. for 3 hours and is then poured into water beforehand and acidified slightly with a 1 mol/L solution of hydrochloric acid, and extracted twice with ethyl acetate. The organic phases obtained are combined and washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to give a brownish oil. This oil is purified by chromatography on silica (eluent: 80/20 heptane/ethyl acetate) to give 950 mg of ethyl 3″-tert-butyl-4″-diethylamino-4′-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]-[1,1′;3′,1″]terphenyl-4-carboxylate (yield=86%) in the form of a colorless oil.

Workup

  1. customIn a 50 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer
  2. extractionextracted twice with ethyl acetate
  3. customThe organic phases obtained
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brownish oil
  9. customThis oil is purified by chromatography on silica (eluent: 80/20 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-b1570dece8d041c5bb849a2393ba10c7
Source dataset
uspto-grants-2012_07
Patent number
US08227507B2

Reaction notes

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