Methylamine → 3-(2-Chloro-4-fluorophenoxy)-N-methyl-1-azetidinecarboxamide

HRID 2371747

Reaction equation

HRID 2371747 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9](Cl)=[O:10])[CH2:6]1.[CH3:17][NH2:18]>O1CCCC1.O>[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]([NH:18][CH3:17])=[O:10])[CH2:6]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 150422343-(2-Chloro-4-fluorophenoxy)-1-azetidinecarbonyl chloride

Product 1

HCID 150422183-(2-Chloro-4-fluorophenoxy)-N-methyl-1-azetidinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.9 g (0.011 mole) of 3-(2-chloro-4-fluorophenoxy)-1-azetidinecarbonyl chloride in 20 mL of tetrahydrofuran was treated with 4 mL (0.05 mole) of 40% aqueous monomethylamine and stirred for 16 hr. The reaction mixture was diluted with 200 mL of water. The solid which precipitated was collected by filtration (2.7 g). The crude product was recrystallized from benzene/ligroin yielding 2.4 g (84.3%) of fine white crystals, mp 139°-141° C.

Workup

  1. customThe solid which precipitated
  2. filtrationwas collected by filtration (2.7 g)
  3. customThe crude product was recrystallized from benzene/ligroin yielding 2.4 g (84.3%) of fine white crystals, mp 139°-141° C.

Sources & evidence

ORD record
ord-b829f53ccb3b417f8b09860b96f2687d
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Linked notes

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