Potassium Carbonate → HCID 57710680, compound

HRID 1982743Notes

Reaction equation

HRID 1982743 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=1)(=[O:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.ClCCl.[Cu].C1COCC1>[C:11]([N:14]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=1)[C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)(=[O:13])[CH3:12]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 87073p-IodocumeneHCID 258025N-[4-(Propan-2-yl)phenyl]ethanimidic acid

Product 1

HCID 57710680HCID 57710680, compound

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 72391,2-DichlorobenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Isopropyliodobenzene (29.2 g, 118 mmol), N-acetyl-4-isopropylaniline (21.0 g, 118 mmol), copper powder (15.0 g, 237 mmol), potassium carbonate (65.4 g, 474 mmol) and 18-crown-6 (2.9 g, 12 mmol) are heated to reflux in 200 ml of 1,2-dichlorobenzene. The reaction is monitored by thin-layer chromatography (eluent: 10% THF in dichloromethane). After 48 h, the still-hot reaction mixture is filtered, the filter residue is washed thoroughly and the solvent is removed on a rotary evaporator. The crude product is chromatographed on silica gel using 10% THF in dichloromethane. The product fractions are concentrated to dryness, recrystallized from hexane and dried under reduced pressure.

Workup

  1. filtrationthe still-hot reaction mixture is filtered
  2. washthe filter residue is washed thoroughly
  3. customthe solvent is removed on a rotary evaporator
  4. customThe crude product is chromatographed on silica gel using 10% THF in dichloromethane
  5. concentrationThe product fractions are concentrated to dryness
  6. customrecrystallized from hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c8ffd424e5bb445fb5f64d0847daecbd
Source dataset
uspto-grants-2009_06
Patent number
US07540978B2

Reaction notes

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