2,6-Xylyl isothiocyanate → N-(2,6-Dimethylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.C(N1CC(OC2C=CC=C(C(F)(F)F)C=2)C1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH3:51])[C:46]=1[N:52]=[C:53]=[S:54]>C(Cl)Cl>[CH3:51][C:47]1[CH:48]=[CH:49][CH:50]=[C:45]([CH3:44])[C:46]=1[NH:52][C:53]([N:9]1[CH2:10][CH:7]([O:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[CH2:8]1)=[S:54]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Crude 3-[3-(trifluoromethyl)phenoxy]azetidine from catalytic debenzylation of 30.0 g (0.078 mole) of 1-benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine was dissolved in 100 ml of methylene chloride and treated dropwise under a nitrogen atmosphere with a solution of 12.7 g (0.078 mole) of 2,6-dimethylphenylisothiocyanate in 25 ml of methylene chloride. The product began to precipitate during the addition and an additional 50 ml of methylene chloride was added to facilitate stirring. After stirring overnight at ambient temperature, the product was collected by filtration (13.5 g, m.p. 196°-199° C.). A 6.0 g sample was recrystallized from isopropanol to give 5.3 g of product, m.p. 197°-199° C.
Workup
- customto precipitate during the addition
- additionan additional 50 ml of methylene chloride was added
- stirringAfter stirring overnight at ambient temperature
- filtrationthe product was collected by filtration (13.5 g, m.p. 196°-199° C.)
- customA 6.0 g sample was recrystallized from isopropanol
Sources & evidence
- ORD record
- ord-0f5c8f17eb164c4eb94013df634e2dd6
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05151418
Reaction notes
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