Methylamine → 3-[2-Fluoro-5-(trifluoromethyl)phenoxy]-N-methyl-1-azetidine-carboxamide

HRID 2371749Notes

Reaction equation

HRID 2371749 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9](Cl)=[O:10])[CH2:6]1.[CH3:20][NH2:21]>O1CCCC1.O>[F:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]([NH:21][CH3:20])=[O:10])[CH2:6]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 150422333-[2-Fluoro-5-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride

Product 1

HCID 150422203-[2-Fluoro-5-(trifluoromethyl)phenoxy]-N-methyl-1-azetidine-carboxamideYield 79.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4.5 g (0.015 mol) of 3-[2-fluoro-5-(trifluoromethyl)phenoxyl]-1-azetidinecarbonyl chloride in 20 mL of tetrahydrofuran was treated with 4.0 g (0.05 mol) of 40% aqueous monomethylamine. After stirring for 16 h the reaction mixture was diluted with 200 mL of water and the oil which separated slowly solidified. The solids were collected by filtration (3.9 g) and recrystallized from benzene/ligroin, yielding 3.5 g (79.8%) of white crystals, mp 93.5°-95° C.

Workup

  1. customthe oil which separated slowly
  2. filtrationThe solids were collected by filtration (3.9 g)
  3. customrecrystallized from benzene/ligroin

Sources & evidence

ORD record
ord-560b5d107b324cb5b43cfb025e680088
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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