1-Hexanethiol → Hexylsulfanylmaleimide

HRID 929387Notes

Reaction equation

HRID 929387 reaction equation
Br[C:2]1[C:3]([NH:5][C:6](=[O:8])[CH:7]=1)=[O:4].C([O-])(=O)C.[Na+].[CH2:14]([SH:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CO>[CH2:14]([S:20][C:2]1[C:3]([NH:5][C:6](=[O:8])[CH:7]=1)=[O:4])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 81061-HexanethiolHCID 517045Sodium AcetateHCID 118195503-bromo-2,5-dihydro-1H-pyrrole-2,5-dione

Product 1

HCID 66927222HexylsulfanylmaleimideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To bromomaleimide (300 mg, 1.69 mmol) and sodium acetate (138 mg, 1.69 mmol) in methanol (60 mL) was added hexanethiol (356 μL, 2.50 mmol). After 5 minutes solvent removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether) afforded 2,3 dihexanethiosuccinimide as a bright yellow paste (13 mg, 0.04 mmol) in 2% and hexylsulfanylmaleimide as a cream powder (alkene 310 mg, 1.46 mmol) in 86% yield.

Workup

  1. customAfter 5 minutes solvent removed in vacuo and purification by flash chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-870ed8da190e4d6b8d717297f4760fa3
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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