Dimethyl Sulfoxide → HCID 21340809, compound

HRID 2184784Notes

Reaction equation

HRID 2184784 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].Br[C:10]([CH3:18])([CH3:17])[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12].CS(C)=O>C(OCC)C>[CH2:7]([O:6][C:4](=[O:5])[CH:3]([N+:1]#[C-:2])[C:10]([CH3:18])([CH3:17])[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH3:8]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 533707Ethyl isocyanoacetateHCID 4524555Allyl 2-bromo-2-methylpropionate

Product 1

HCID 21340809HCID 21340809, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl isocyanoacetate (2.19 g, 19.4 mmol) and allyl 2-bromo-2-methylpropionate (4.40 g, 21.3 mmol) are dissolved in diethyl ether (50 mL) and methyl sulfoxide (50 mL) with stirring. In a separate flask sodium hydride (775 mg of 60% dispersion in mineral oil) is rinsed with hexane and suspended in diethyl ether (10 mL). The suspension is added dropwise to the stirring solution and an additional methyl sulfoxide (50 mL) is added to the mixture. The reaction is stirred for 2 hours at room temperature. The mixture is diluted with diethyl ether (250 mL) and washed several times with water. The organic phase is dried over sodium sulfate and evaporated to give 3-isocyano-2,2-dimethyl-succinic acid 1-allyl ester 4-ethyl ester.

Workup

  1. washIn a separate flask sodium hydride (775 mg of 60% dispersion in mineral oil) is rinsed with hexane
  2. additionThe suspension is added dropwise to the stirring solution
  3. additionan additional methyl sulfoxide (50 mL) is added to the mixture
  4. additionThe mixture is diluted with diethyl ether (250 mL)
  5. washwashed several times with water
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-410b6620ee4b47849cac6ced6cbc0273
Source dataset
uspto-grants-2002_06
Patent number
US06399598B1

Reaction notes

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