Methylamine → 3-(3,4-Dichlorophenoxy)-N-methylazetidine-1-carboxamide

HRID 2371750Notes

Reaction equation

HRID 2371750 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.[CH3:17][NH2:18]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10]([NH:18][CH3:17])=[O:11])[CH2:7]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15042235HCID 15042235, compound

Product 1

HCID 150422213-(3,4-Dichlorophenoxy)-N-methylazetidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.6 g (0.02 mole) of 3-(3,4-dichlorophenoxy)-1-azetidinecarbonyl chloride in 20 mL of tetrahydrofuran was stirred while 5 mL (0.06 mole) of 40% aqueous methylamine was added slowly and stirring was continued for 18 h. The reaction mixture was diluted with 200 mL of ice water, and the solid which formed was collected by filtration (6.9 g). The crude wet solid was recrystallized from ethanol/water to yield 3.65 g (66.3%) of greenish-gray plate-like crystals, mp 158°-159° C.

Workup

  1. additionwas added slowly
  2. customthe solid which formed
  3. filtrationwas collected by filtration (6.9 g)
  4. customThe crude wet solid was recrystallized from ethanol/water
  5. customto yield 3.65 g (66.3%) of greenish-gray plate-like crystals, mp 158°-159° C.

Sources & evidence

ORD record
ord-636895cb3c4a43f6b5b9290e1b1be84b
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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