Sodium Iodide → HCID 67324610, compound

HRID 1257582Notes

Reaction equation

HRID 1257582 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:4]=1[CH2:5][NH:6][C:7](=[O:10])[CH2:8]Cl.[I-:17].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:4]=1[CH2:5][NH:6][C:7](=[O:10])[CH2:8][I:17]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 16495703HCID 16495703, compound

Product 1

HCID 67324610HCID 67324610, compoundYield 132.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(2,4-Dimethoxy-benzyl)-2-chloro-acetamide (2.2074 g, 9.0584 mmol) in acetone (20 mL) was added sodium iodide (4.121 g, 27.49 mmol). The reaction mixture was stirred at 50° C. for two hours, and then filtered to remove inorganic salts. The filtrate was evaporated in vacuo, re-suspended in ethyl acetate, and filtered again. The filtrate was evaporated in vacuo to provide 4.01 g of N-(2,4-Dimethoxy-benzyl)-2-iodo-acetamide, which was carried forward without purification. LCMS (Method E, ESI): RT=1.46 min, m+H=336.2; 1H NMR (400 MHz, CDCl3) δ: 7.17 (d, J=8.2, 1H), 6.55 (s, 1H), 6.47 (d, J=2.2, 1H), 6.44 (dd, J=8.2, 2.3, 1H), 4.36 (d, J=5.8, 2H), 3.85 (s, 3H), 3.80 (s, 3H), 3.68 (s, 2H).

Workup

  1. filtrationfiltered
  2. customto remove inorganic salts
  3. customThe filtrate was evaporated in vacuo
  4. filtrationfiltered again
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-b06722ffcfa34021aae5143364ba8204
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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