Methylamine → Cis N,2-Dimethyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 974647Notes

Reaction equation

HRID 974647 reaction equation
[CH3:1][CH:2]1[CH:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][N:3]1[C:17](Cl)=[O:18].[CH3:20][NH2:21]>O1CCCC1.O>[CH3:20][NH:21][C:17]([N:3]1[CH2:4][C@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[C@@H:2]1[CH3:1])=[O:18]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 197996032-Methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride

Product 1

HCID 70361156Cis N,2-Dimethyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.02 g (0.01 mole) of crude (73%) 2-methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride cis isomer in 20 ml of tetrahydrofuran was treated while stirring with 1.6 g (0.02 mole) of 40% aqueous monomethylamine. After stirring for 6 hr, the reaction mixture was diluted with 100 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo (4.2 g). The oil solidified on standing and was recrystallized from isooctane with a trace of benzene to give 2.6 g (90.3%) of white crystalline product, m.p. 89°-91° C.

Workup

  1. additionwas treated
  2. customthe oil which separated
  3. extractionwas extracted into methylene chloride (2×50 ml)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo (4.2 g)
  6. customwas recrystallized from isooctane with a trace of benzene

Sources & evidence

ORD record
ord-28ed1b3b86ac422dbf739283c6091dce
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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