Iodine → HCID 135890114, compound

HRID 539887Notes

Reaction equation

HRID 539887 reaction equation
[CH:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[C:14]([S:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=2[O:26][CH2:27][CH2:28][CH3:29])[NH:7][C:6](=[O:30])[CH:5]=1)([CH3:3])[CH3:2].[I:31]I>[N+]([O-])([O-])=O.[Ag+].CO>[I:31][C:5]1[C:6](=[O:30])[NH:7][C:8]([C:10]2[CH:15]=[C:14]([S:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=2[O:26][CH2:27][CH2:28][CH3:29])=[N:9][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 807IodineHCID 136236333HCID 136236333, compound

Product 1

HCID 135890114HCID 135890114, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 887MethanolSolvent

Procedure

The compound (1.69 g, 3.9 mmol) of example 1 was added into methanol (15 ml), and added with silver nitrate (0.66 g, 3.9 mol), and then with I2 grain (0.98 g, 3.9 mmol) under stirring. The reaction mixture was stirred at room temperature for 0.5 h, and TLC showed that the reaction was complete. The reaction mixture was filtered, and the filtrate was concentrated. The concentrate was washed with water, extracted with dichloromethane. The organic layer was washed with saturated saline, dried with anhydrous sodium sulfate, and concentrated. The residue was recrystallized from ethyl acetate to give a yellowish solid (1.52 g, yield: 70%). 1H NMR (CDCl3) δ: 8.90 (1H, d), 7.89 (1H, dd), 7.16 (1H, d), 4.27 (2H, t), 3.46 (1H, m), 3.08 (4H, t), 2.49 (4H, t), 2.27 (3H, s), 2.03 (2H, m), 1.25 (6H, d), 1.16 (3H, t).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe concentrate was washed with water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-11b00addbc8b4c1ab985cc8513f6fffc
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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