Potassium Carbonate → Phthalimide

HRID 2055143Notes

Reaction equation

HRID 2055143 reaction equation
ClC1N=CC(C2N=CN(CCCC[N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])C=2)=CC=1.N1C=C(C2C=CC(Cl)=NC=2)N=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCN1C(=O)C2=CC=CC=C2C1=O>CN(C=O)C>[C:18]1(=[O:27])[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25](=[O:26])[NH:17]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 11559963HCID 11559963, compoundHCID 178477962HCID 178477962, compound

Product 1

HCID 6809PhthalimideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-[4-(6-chloro-pyridin-3-yl)-imidazol-1-yl]-butyl)-isoindole-1,3-dione. To a solution of 5-(1H-imidazol-4-yl)-2-chloro-pyridine (15.14 g, 84.1 mmoles) in DMF (336 ml) was added potassium carbonate (58.1 g, 420.6 mmoles) and N-(4-bromobutyl)phthalimide (59.3 g, 210.3 mmoles) at room temperature under dry conditions. The solution was left stirring at room temperature for 48 hours. The reaction was filtered and the resulting clear solution was dumped onto ice (1.5 L). The precipitate was filtered and rinsed with water (2×500 ml) and was pumped on for 1 hour. The material was than rinsed with diethyl ether (15×500 ml) and than was pumped on to yield 2-14-[4-(6-chloro-pyridin-3-yl)-imidazol-1-yl]-butyl)-isoindole-1,3-dione (25.16 g, 78%). MH+(381)

Workup

  1. waitThe solution was left
  2. filtrationThe reaction was filtered
  3. filtrationThe precipitate was filtered
  4. washrinsed with water (2×500 ml)
  5. customwas pumped on for 1 hour
  6. washthan rinsed with diethyl ether (15×500 ml)

Sources & evidence

ORD record
ord-3c831d86f1324ac6bea02769f52d21fa
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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