1-Hexanethiol → N-Methyl hexylsulfanylmaleimide

HRID 929386Notes

Reaction equation

HRID 929386 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4](Br)[C:3]1=[O:9].O.O.O.C([O-])(=O)C.[Na+].[CH2:18]([SH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CO>[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([S:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:3]1=[O:9]

Participants

5

Reactant 3

HCID 81061-HexanethiolHCID 12136311N-methyl bromomaleimideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 68150143N-Methyl hexylsulfanylmaleimideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To N-methyl bromomaleimide (100 mg, 0.53 mmol) and sodium acetate trihydrate (70 mg, 0.53 mmol) in methanol (15 mL) was added hexanethiol (74 μL, 0.58 mmol) in methanol (100 mL) dropwise over 1 hour with vigorous stirring. After 5 minutes solvent was removed in vacuo. Purification by column chromatography (gradient elution in 10% ethyl acetate in petroleum ether to 30% ethyl acetate in petroleum ether) afforded the desired compound as a bright yellow solid (99 mg, 0.44 mmol) in 83% yield. δH (600 MHz, CDCl3) 6.03 (s, 1H, H-2), 3.01 (s, 3H, H3-5), 2.89 (t, 2H, J=7.6, 2H, H2-11), 1.76-1.71 (m, 2H, H2-10), 1.46-1.41 (m, 2H, H2-9), 1.33-1.27 (m, 4H, H2-7 and CH2-8), 0.89 (t, 3H, J=6.5, H3-6); δC (125 MHz, CDCl3) 171.47 (C═O), 169.94 (C═O), 151.84 (C3), 117.27 (C2), 31.92 (C11), 31.31 (CH2), 28.64 (CH2), 27.75 (CH2), 24.10 (C5), 24.10 (C7), 14.09 (C6); IR (oil, cm−1) 2727 (w), 1708 (s); MS (FAB+) m/z (relative intensity): 250 ([M+Na], 40), 228 (35), 199 (30), 176 (100); Exact Mass Calcd for [C11H17NO2S]+Na requires m/z 250.0878 Found 250.0880 (FAB+).

Workup

  1. customAfter 5 minutes solvent was removed in vacuo
  2. customPurification
  3. washby column chromatography (gradient elution in 10% ethyl acetate in petroleum ether to 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-dcb89c9dc4a74dd2a5ce2596ad76f312
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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