Potassium Carbonate → HCID 13595971, compound

HRID 1630813Notes

Reaction equation

HRID 1630813 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH2:5])=[O:4].[C:8](=O)([O-])[O-:9].[K+].[K+]>CC(C)=O>[OH:9][CH2:8][NH:5][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12957Trimethylacetamide

Product 1

HCID 13595971HCID 13595971, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

A flask is charged with 2,2-dimethyl-propionamide (1.00 g, 9.98 mmol), p-formaldehyde (0.736 g, 9.98 mmol), and potassium carbonate (0.054 g, 3.95 mmol). The reaction mixture is stirred at 75° C. for 16 h, whereupon it is cooled to room temperature and diluted with acetone. Filtration and concentration of the filtrate give a residue which is purified by silica gel flash chromatography (heptane-ethyl acetate, 4:1) to afford N-hydroxymethyl-2,2-dimethyl-propionamide as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (s, 9H), 4.73 (d, J=7.1 Hz, 2H).

Workup

  1. temperatureis cooled to room temperature
  2. filtrationFiltration and concentration of the filtrate
  3. customgive a residue which
  4. customis purified by silica gel flash chromatography (heptane-ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-aa09a2f7a97a4c4fb661c1fc4c389d2b
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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