Methyl iodide → 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-thiopropionimidic acid methyl ester hydroiodide

HRID 1621099Notes

Reaction equation

HRID 1621099 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]([NH2:16])=[S:15].[I:17][CH3:18]>CC(C)=O>[IH:17].[CH3:18][S:15][C:14](=[NH:16])[CH2:13][CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 9696783-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanethioamide

Product 1

HCID 866774803-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-thiopropionimidic acid methyl ester hydroiodideYield 67.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-thiopropionamide (2.13 g, 9.09 mmol) in acetone (30 mL) was added iodomethane (3.87 g, 1.71 mL, 27.3 mmol) at r. t. under a nitrogen atmosphere. The reaction mixture was stirred at RT for 48 h and the obtained suspension was filtered, washed with diethyl ether and dried in vacuo to give the product as light yellow solid (2.3 g, 6.11 mmol, 67.2%). MS: M=249.1 (M+H)+

Workup

  1. filtrationthe obtained suspension was filtered
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-74b4fc3688f0480aafc3827e0f4a5e57
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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