Dimethyl Sulfide → HCID 57428875, compound

HRID 507682Notes

Reaction equation

HRID 507682 reaction equation
N[C@H](C(O)=O)C[SeH].[Li]CCCC.CN(C)CCN(C)C.[CH2:21]([N:23]([CH2:34][CH3:35])[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[CH3:22].[CH3:36][S:37]C>C1COCC1>[CH2:34]([N:23]([CH2:21][CH3:22])[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[S:37][CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 231459N,N-Diethyl-para-anisamideHCID 178511841HCID 178511841, compound

Product 1

HCID 57428875HCID 57428875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sec-BuLi (1.4 M in cyclohexane, 11.34 mL, 15 mmol) was carefully added to a mixture of N,N,N′,N′-tetramethylethane-1,2-diamine (2.2 mL, 15 mmol) in anhydrous THF at −78° C. N,N-Diethyl-4-methoxybenzamide (3 g, 14.4 mmol) dissolved in 5 mL of anhydrous THF was added dropwise to the reaction mixture which was allowed to stir for 1 h Dimethyl sulfide (2.5 mL, 28.8 mmol) was then added to the reaction. After stirring for 15 min, the cooling bath was removed and the mixture was stirred overnight. The reaction was diluted with ethyl acetate and washed with a solution of saturated sodium bicarbonate, water and then brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 20 to 80% ethyl acetate in hexanes to obtain the product as a light yellow oil. Yield=2.51 g. MS (M+H)+ 254.

Workup

  1. additionwas added dropwise to the reaction mixture which
  2. additionwas then added to the reaction
  3. customthe cooling bath was removed
  4. stirringthe mixture was stirred overnight
  5. additionThe reaction was diluted with ethyl acetate
  6. washwashed with a solution of saturated sodium bicarbonate, water
  7. dry with materialThe organic layer was then dried with sodium sulfate
  8. concentrationconcentrated
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9eaf5759cfb642039848c8751e9e1b0f
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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