Hydrochloric Acid → Methyl 2-cyano-3-[(2,2-dimethylpropanoyl)amino]-3-(methylsulfanyl)prop-2-enoate

HRID 2192838Notes

Reaction equation

HRID 2192838 reaction equation
[C:1]([C:3](=[C:8](SC)[S:9][CH3:10])[C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH3:13][C:14]([CH3:19])([CH3:18])[C:15]([NH2:17])=[O:16].[H-].[Na+].Cl>CC(N(C)C)=O>[C:1]([C:3](=[C:8]([NH:17][C:15](=[O:16])[C:14]([CH3:19])([CH3:18])[CH3:13])[S:9][CH3:10])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12957TrimethylacetamideHCID 24758Sodium hydrideHCID 319957Methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate

Product 1

HCID 72342760Methyl 2-cyano-3-[(2,2-dimethylpropanoyl)amino]-3-(methylsulfanyl)prop-2-enoateYield 46.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate (4.06 g) and 2,2-dimethylpropanamide (2.02 g) were dissolved in DMA (200 ml), and sodium hydride (1.92 g) was added under ice-cooling. The mixture was stirred at room temperature overnight, and poured into ice. The mixture was acidified with 1 N aqueous hydrochloric acid solution. The precipitated crystals were collected by filtration, and dried to give the object compound (2.4 g).

Workup

  1. temperaturecooling
  2. additionpoured into ice
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-caf6c36d25b44726b5ded8064fdef22b
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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