Potassium Carbonate → HCID 86646688, compound

HRID 1677438Notes

Reaction equation

HRID 1677438 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=O.[CH3:10][O:11][NH:12][CH3:13].Cl.C([O-])([O-])=O.[K+].[K+]>S(Cl)(Cl)=O>[CH3:1][O:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([N:12]([O:11][CH3:10])[CH3:13])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 30175063-Methoxy-2,2-dimethylpropanoic acid

Product 1

HCID 86646688HCID 86646688, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-methoxy-2,2-dimethyl-propionic acid (1.0 g, 7.6 mmol) in thionyl chloride (5 ml) was heated to 50° C. for 16 hours. The reaction mixture was concentrated to a yellow residue and then dissolved in DCM (15 ml). O,N-Dimethyl-hydroxylamine-hydrogen chloride (886 mg, 9.1 mmol) and powdered K2CO3 (2.2 g, 16 mmol) were added, and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered through a filter funnel, and the filtrate was collected and concentrated giving a white semisolid. The crude product was purified by silica gel chromatography using 20-50% EtOAc in hexanes as eluant providing 260 mg (20%) of 3,N-dimethoxy-2,2,N-trimethyl-propionamide as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated to a yellow residue
  2. dissolutiondissolved in DCM (15 ml)
  3. filtrationThe reaction mixture was filtered through a filter funnel
  4. customthe filtrate was collected
  5. concentrationconcentrated
  6. customgiving a white semisolid
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7def7262a2e44fc1a7c871525ebd1110
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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