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

HRID 1886643Notes

Reaction equation

HRID 1886643 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, stirring was continued for 18 hr. 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, m.p. 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, m.p. 158°-159° C.

Sources & evidence

ORD record
ord-b6dd48fd514a4de6b18148be12178def
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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