Acetamide → Acetanilide

HRID 1243067Notes

Reaction equation

HRID 1243067 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1NC.IC1C=CC=CC=1.CCCCCCCCCCCC>[Cu]I.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:15]1([NH:4][C:1](=[O:3])[CH3:2])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

9

Reactant 5

HCID 178AcetamideHCID 8182DodecaneHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 904AcetanilideYield 100%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A 15 mL resealable Schlenk tube was charged with CuI (10 mg, 0.0525 mmol, 5.0 mol %), acetamide (170 mg, 2.88 mmol), K3PO4 (450 mg, 2.12 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (17 μL, 0.108 mmol, 10 mol %), iodobenzene (115 μL, 1.03 mmol) and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 60° C. for 4 h. After the resulting suspension was allowed to reach room temperature, ethyl acetate (1 mL) and dodecane (235 μL, internal GC standard) were added. GC analysis indicated 100% yield of the desired product.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature

Sources & evidence

ORD record
ord-7c914e2822254b4c91a83325f0dde817
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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