Methyl iodide → Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide

HRID 2747Notes

Reaction equation

HRID 2747 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:25])#[N:2].CI.[C:31]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([N:12]([CH3:31])[S:13]([C:16]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:25])#[N:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15886959Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Product 1

HCID 54408439Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamideYield 96.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzo[b]thiophene-2-sulfonic acid [1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.61 mmol) in 3 mL of DMF is added methyl iodide (0.13 g, 0.91 mmol) followed by K2CO3 (0.13 g, 0.91 mmol). The solution is stirred at ambient temperatures for 6 h. After this time, the solution is diluted with H2O and EtOAc. The layers are separated. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is triturated with Et2O to give the title compound (0.25 g, 0.59 mmol) as a white solid.

Workup

  1. customThe layers are separated
  2. washThe organic layer is washed with H2O and saturated NaCl
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is triturated with Et2O

Sources & evidence

ORD record
ord-f4e8e6ec20fc45b7ba597aed2b56cab8
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Reaction notes

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