Dimethyl Disulfide → HCID 68689982, compound

HRID 1159065Notes

Reaction equation

HRID 1159065 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)[CH3:2].C([Li])(CC)C.[CH3:22][S:23]SC>C1COCC1>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][C:6]=1[S:23][CH3:22])[CH3:16]

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 47717594N,N-Diethyl-4-propylbenzamideHCID 178418400CID 53628100

Product 1

HCID 68689982HCID 68689982, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of N,N-diethyl-4-propylbenzamide (2.0 g, 9.3 mmol) and N,N,N′N′-tetramethylethylenediamine (1085 mg, 9.4 mmol) in dry THF (93 mL) at −78° C. under Ar was added 0.78 M s-butyllithium in hexanes (12 mL). The reaction was stirred for 30 min and then methyl disulfide (1936 mg, 12.1 mmol) was added. The reaction was stirred for 5 min and then quenched with MeOH (1 mL) and brine. The reaction was extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and conc in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 0-30% EtOAc in hexanes) to yield 2.1 g (86%) of the product as a yellow oil. MS (ESI) 266 (M+H).

Workup

  1. stirringThe reaction was stirred for 5 min
  2. customquenched with MeOH (1 mL) and brine
  3. extractionThe reaction was extracted with EtOAc (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (SiO2, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b3e2c20702664f5f80637e6645285ecf
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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