Water → 3-Butyl-5,5-dimethylthiazolidin-2-imine

HRID 1693630Notes

Reaction equation

HRID 1693630 reaction equation
[CH3:1][C:2]1([CH3:5])[CH2:4][S:3]1.[CH2:6]([NH:10][C:11]#[N:12])[CH2:7][CH2:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[CH2:6]([N:10]1[CH2:4][C:2]([CH3:1])([CH3:5])[S:3][C:11]1=[NH:12])[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1380502,2-DimethylthiiraneHCID 12295218Butylcyanamide

Product 1

HCID 666431113-Butyl-5,5-dimethylthiazolidin-2-imineYield 66.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,2-dimethyl-thiirane (TCI) (1.5 g, 17 mmol), N-butyl-cyanamide (1.7 g, 17 mmol) (prepared as described in Ross J. Med. Chem. 1979, 22; 412) and potassium carbonate (2.4 g, 17 mmol) in 2-butanone (15 mL) was heated to 80° C. overnight. The mixture was poured into water, and extracted with ethyl acetate (2×). The combined organic extracts were dried over Na2SO4, filtered, concentrated under reduced pressure to afford 2.11 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e254a6fc0c843869489b23d36051ec6
Source dataset
uspto-grants-2012_04
Patent number
US08158663B2

Reaction notes

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