Triethylamine → 4-((2-Mercaptoethylthio)methyl)-4-methyloxazolidin-2-one

HRID 1023484Notes

Reaction equation

HRID 1023484 reaction equation
Cl[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.[CH2:10]([SH:13])[CH2:11][SH:12].C(N(CC)CC)C>CN(C=O)C>[SH:12][CH2:11][CH2:10][S:13][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109021,2-EthanedithiolHCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

Product 1

HCID 593551744-((2-Mercaptoethylthio)methyl)-4-methyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (1.85 g, 12.4 mmol) in DMF (5 ml) was added 1,2-ethanedithiol (10.0 ml, 119 mmol). Triethylamine (2.0 ml, 14 mmol) was added, and the solution heated to 90° C. for 2 h, then cooled to RT and concentrated in vacuo. Purification of the residue by flash chromatography (30%→80% EtOAc in hexanes) afforded a mixture of the title compound and various EDT disulfide adducts which was used without further purification. ESI/APCI expected for C7H13NO2S2: 207.04. Found: 208 (MH+), 300 (MH++EDT), 414 (MNa++2 EDT).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue by flash chromatography (30%→80% EtOAc in hexanes)
  4. customafforded

Sources & evidence

ORD record
ord-000747e134654dc192b9f9fdcd33cbe1
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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