Hydrochloric Acid → HCID 2452159, compound

HRID 2299249Notes

Reaction equation

HRID 2299249 reaction equation
[CH3:1][NH2:2].Cl[CH2:4][C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15])=[O:6].Cl>C1COCC1.CCOC(C)=O>[CH3:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=1[NH:7][C:5](=[O:6])[CH2:4][NH:2][CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6329Methylamine2×HCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 2452159HCID 2452159, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, methylamine (600 mmols) in 300 mL THF was cooled to 0° C. A solution of 2-chloro-N-(2′,6′-dimethylphenyl)acetamide (100 mmols) was dissolved in 200 mL THF, and slowly dripped into the cold methylamine solution. The reaction was stirred overnight. The reaction was filtered, and the filtrate evaporated to yield an oily residue. This was dissolved in EtOAc (100 mL) and treated with 1N HCl (200 mL). The aqueous layer was washed with EtOAc, then basified to Ph 10-12 with 6 N NaOH. The product was extracted into EtOAc (2×50 mL), the organic phase was dried, and the solvent was evaporated to yield N-(2,6-dimethyl-phenyl)-2-methylamino-acetamide (compound (23)) as an oil (12.8 gm; 67% yield).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated
  3. customto yield an oily residue
  4. washThe aqueous layer was washed with EtOAc
  5. extractionThe product was extracted into EtOAc (2×50 mL)
  6. customthe organic phase was dried
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-997ff809253f4bf9be0c9132adc36c87
Source dataset
uspto-grants-2002_12
Patent number
US06495681B1

Reaction notes

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