4'-Bromoacetanilide → N-[4-(Hexylamino)phenyl]acetamide

HRID 1354976Notes

Reaction equation

HRID 1354976 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][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]([NH:4][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:2](=[O:3])[CH3:1])=[CH:6][CH:7]=1)[CH2:6][CH2:7][CH2:14][CH2:13][CH3:16]

Participants

5

Reactant 2

HCID 76834'-BromoacetanilideHCID 23676156Sodium t-butoxide

Product 1

HCID 22257031N-[4-(Hexylamino)phenyl]acetamideYield 162.2%

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-di-cyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (11.9 mg, 0.025 mmol), 4-bromoacetanilide (107 mg, 0.5 mmol) and sodium tbutoxide (120 mg, 1.2 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. nHexylamine (100 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 110° C. The reaction mixture was stirred for 3 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 1:1 hexane:ethyl acetate gave 95 mg (81%) of the title compound as a white solid.

Workup

  1. additionAn oven-dried resealable schlenk tube containing a stir bar
  2. customThe tube was capped with a rubber septum
  3. customevacuated
  4. additionnHexylamine (100 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 110° C
  8. customquenched with water
  9. extractionExtraction with ethyl acetate three times

Sources & evidence

ORD record
ord-cf3a3ff627204c948afdbf5d5f9e4378
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

Loading…