Potassium Carbonate → Phthalimide

HRID 2055149Notes

Reaction equation

HRID 2055149 reaction equation
COC1N=CC(C2N=C(C)NC=2CCCC[N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])=CC=1.COC1C=CC(C2N=C(C)NC=2)=CN=1.C(=O)([O-])[O-].[K+].[K+].BrCCCCN1C(=O)C2=CC=CC=C2C1=O>CN(C=O)C>[C:19]1(=[O:28])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26](=[O:27])[NH:18]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 69223233HCID 69223233, compoundHCID 178488784HCID 178488784, compound

Product 1

HCID 6809PhthalimideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{4-[4-(6-methoxy(3-pyridyl))-2-methylimidazolyl]butyl}-isoindole-1,3-dione. To a solution of 2-methoxy-5-(2-methylimidazol-4-yl)pyridine (5.0 g, 26.4 mmoles) in DMF (100 ml) was added potassium carbonate (18.3 g, 132 mmoles) and N-(4-bromobutyl)phthalimide (8.97 g, 31.7 mmoles) at room temperature under dry conditions. The solution was left stirring at room temperature for 72 hours. The reaction was filtered and the resulting clear solution was dumped onto ice (1 L). The precipitate was filtered and rinsed with water (2×200 ml) and was pumped on for 1 hour. The material was than rinsed with diethyl ether (7×200 ml) and than was pumped on to yield to yield 2-14-[4-(6-methoxy(3-pyridyl))-2-methylimidazolyl]butyl}-isoindole-1,3-dione (4.1 g, 48%). MH+(391)

Workup

  1. waitThe solution was left
  2. filtrationThe reaction was filtered
  3. filtrationThe precipitate was filtered
  4. washrinsed with water (2×200 ml)
  5. customwas pumped on for 1 hour
  6. washthan rinsed with diethyl ether (7×200 ml)
  7. customto yield

Sources & evidence

ORD record
ord-e56027f3da9f404d87130de205de0e10
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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