Sodium Carbonate → 4-Amino-3-iodo-n-methylbenzeneacetamide

HRID 129517Notes

Reaction equation

HRID 129517 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10]C=C2.[I:15]Cl.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[NH2:10][C:11]1[CH:12]=[CH:13][C:5]([CH2:4][C:3]([NH:2][CH3:1])=[O:14])=[CH:6][C:7]=1[I:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24640Iodine chlorideHCID 15391297N-Methyl-1H-indole-5-acetamide

Product 1

HCID 233658104-Amino-3-iodo-n-methylbenzeneacetamideYield 63.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Amino-N-methyl-benzeneacetamide (6) (6.56 g, 0.04 mol) was dissolved in CH3CN (200 mL) and ICl (7.14 g dissolved in 60 mL of CH3CN, 0.044 mol) was added dropwise with vigorous stirring. After stirring at RT for 3 h, saturated aqueous Na2CO3 (50 mL) was added and the reaction was concentrated in vacuo. The residue was dissolved in EtOAc and extracted with saturated aqueous Na2CO3. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product (7) (7.38 g, 63.6%) was isolated from the concentrate by trituration with CH2Cl2 /EtOAc and washing with Et2O. This material was found to be pure by NMR analysis.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. extractionextracted with saturated aqueous Na2CO3
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-000897cba7904252aaa17747d39b4be9
Source dataset
uspto-grants-1995_11
Patent number
US05468768

Reaction notes

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