Ethanol → HCID 57538790, compound

HRID 642556Notes

Reaction equation

HRID 642556 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH2:5])=[S:4].Cl[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:15](O)[CH3:16]>>[CH2:13]([O:12][C:10]([C:9]1[S:4][C:3]([C:2]([CH3:7])([CH3:6])[CH3:1])=[N:5][C:15]=1[CH3:16])=[O:11])[CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 7751Ethyl chloroacetateHCID 30311302,2-Dimethylpropanethioamide

Product 1

HCID 57538790HCID 57538790, compound

Procedure

A solution of 2,2-dimethyl-thiopropionamide (7.7 g, 65.8 mmol) and ethyl 2-chloroacetate (9.26 mL, 67 mmol) in 150 mL of ethanol was heated at reflux temperature for 24 h. The reaction mixture was concentrated under reduced pressure, suspended in ethyl acetate, and washed with saturated aqueous sodium bicarbonate and brine solutions. The organic fraction was dried over anhydrous magnesium sulfate and concentrated to 14.1 g of an orange viscous material. MS (ESI+): 229.4 (M+1).

Workup

  1. temperatureat reflux temperature for 24 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washwashed with saturated aqueous sodium bicarbonate and brine solutions
  4. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to 14.1 g of an orange viscous material

Sources & evidence

ORD record
ord-7e29b5ae4fc64fb8997fd0f7062ef90b
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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