3-Chloroacetanilide → N-[3-(Dibutylamino)phenyl]acetamide

HRID 1354980Notes

Reaction equation

HRID 1354980 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Cl)[CH:6]=1)=[O:3].C[C:13]([CH3:16])([O-])[CH3:14].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[CH2:5]([N:4]([CH2:2][CH2:14][CH2:13][CH3:16])[C:7]1[CH:6]=[C:5]([NH:4][C:2](=[O:3])[CH3:1])[CH:10]=[CH:9][CH:8]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 114933-ChloroacetanilideHCID 23676156Sodium t-butoxide

Product 1

HCID 13879300N-[3-(Dibutylamino)phenyl]acetamideYield 161.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst

Procedure

An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (11.9 mg, 0.025 mmol), 3-chloroacetanilide (85 mg, 0.5 mmol) and sodium tbutoxide (120 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. Dinbutylamine (126 μL, 0.75 mmol) and tbutanol (1 mL) were added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 90° C. The reaction mixture was stirred for 18 h, allowed to cool down to room temperature and quenched with water. Extraction with ethyl acetate three times followed by chromatography on silica gel column with 4:1 hexane:ethyl acetate gave 106 mg (81%) of the title compound as a pale yellow oil.

Workup

  1. additionAn oven-dried resealable schlenk tube containing a stir bar
  2. customThe tube was capped with a rubber septum
  3. customevacuated
  4. additionDinbutylamine (126 μL, 0.75 mmol) and tbutanol (1 mL) were added through the septum via syringe
  5. customscrew cap
  6. customThe schlenk tube was sealed
  7. customput into a pre-heated oil bath at 90° C
  8. customquenched with water
  9. extractionExtraction with ethyl acetate three times

Sources & evidence

ORD record
ord-5e83fbd8bb524de3bab2ce767bba3562
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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