4-Chloroaniline → HCID 23132421, compound

HRID 2097363Notes

Reaction equation

HRID 2097363 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.BrCCCCCC[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=O.[C:27]([O-:30])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:4][CH2:3][CH2:2][CH2:8][CH2:7][CH2:17][C:18]23[CH:25]=[CH:24][CH:23]=[CH:22][CH:19]2[C:20]([NH:16][C:27]3=[O:30])=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 11430Potassium CarbonateHCID 141120N-(6-Bromohexyl)phthalimide

Product 1

HCID 23132421HCID 23132421, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloroaniline (2.55 g, 20 mmol), N-(6-bromohexyl)-phthalimide (6.20 g, 20 mmol) and K2CO3 (2.76 g, 20 mmol) were suspended in DMF (50 mL) under an atmosphere of argon and stirred at 90° C. for 25 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water (100 mL) and Et2O (100 mL). The aqueous layer was extracted with Et2O (2×50 mL), the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (EtOAc/hexane 1:6 to 1:3) to give the title compound (3.41 g), together with some 4-chloroaniline (≈2:1).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water (100 mL) and Et2O (100 mL)
  3. extractionThe aqueous layer was extracted with Et2O (2×50 mL)
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography (EtOAc/hexane 1:6 to 1:3)

Sources & evidence

ORD record
ord-340d87f9dac943f5b403772e6d0f9017
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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