Dimethylamine → 3-(2-Chloro-6-methylphenoxy)-N,N-dimethyl-1-azetidinecarboxamide

HRID 2371745Notes

Reaction equation

HRID 2371745 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9](Cl)=[O:10])[CH2:6]1.[CH3:17][NH:18][CH3:19]>O1CCCC1.O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]([N:18]([CH3:19])[CH3:17])=[O:10])[CH2:6]1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 150422313-(2-Chloro-6-methylphenoxy)-1-azetidinecarbonyl chloride

Product 1

HCID 199062203-(2-Chloro-6-methylphenoxy)-N,N-dimethyl-1-azetidinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3.9 g (0.015 mole) of 3-(2-chloro-6-methylphenoxy)-1-azetidinecarbonyl chloride in 20 mL of tetrahydrofuran was treated all at once with 5.1 mL (0.045 mole) of 40% aqueous dimethylamine. After stirring for 72 h the raction mixture was diluted with 200 mL of water and the oil which separated was extracted into methylene chloride (3×30 mL). The combined extracts were dried by filtering through Whatman PS paper and concentrated in vacuo (3.6 g). The crude oil solidified when cooled in a dry ice/acetone bath and was recrystallized from ethyl ether in a dry ice-acetone bath yielding, after filtering cold, 2.6 g (64.5%) of coarse white crystals, mp 46°-47° C.

Workup

  1. customthe oil which separated
  2. extractionwas extracted into methylene chloride (3×30 mL)
  3. customThe combined extracts were dried
  4. filtrationby filtering through Whatman PS paper
  5. concentrationconcentrated in vacuo (3.6 g)
  6. temperaturecooled in a dry ice/acetone bath
  7. customwas recrystallized from ethyl ether in a dry ice-acetone bath
  8. customyielding
  9. filtrationafter filtering cold

Sources & evidence

ORD record
ord-93fc2324eaff467195c451fec22d493d
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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