N-Iodosuccinimide → HCID 71008151, compound

HRID 877019Notes

Reaction equation

HRID 877019 reaction equation
[CH3:1][N:2]1[C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[I:15]N1C(=O)CCC1=O>B(F)(F)F.CCOCC.O>[I:15][C:10]1[C:6]2[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:7]=2[S:8][C:9]=1[CH3:11]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 14638935HCID 14638935, compound

Product 1

HCID 71008151HCID 71008151, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8000Boron trifluoride etherateSolvent

Procedure

To a stirred solution of Step 4 intermediate (12.5 g, 59.52 mmol) in boron trifluoride diethyl etherate (300 ml) was added N-iodosuccinimide (19.9 g, 89.28 mmol) and the mixture was stirred for 3 h at room temperature under nitrogen atmosphere. The reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (3×200 ml) and the combined organic layers were washed with water (2×150 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 2% ethyl acetate in chloroform to obtain 9.7 g of the product as a pale brown solid; 1H NMR (300 MHz, DMSO-d6) δ 2.37 (s, 3H), 3.21 (s, 3H), 3.42 (s, 3H); MS (m/z) 337.11 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. washthe combined organic layers were washed with water (2×150 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a49e088dac0c40da9e6e61e577c4f2be
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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