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2,6-Xylyl isothiocyanate → N-(2,6-Dimethylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide

HRID 974551
Notes
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Reaction equation

HRID 974551 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 879762,6-Xylyl isothiocyanateHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidineHCID 117286941-Benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 15053383N-(2,6-Dimethylphenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

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 addition 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

  1. customto precipitate during the addition
  2. additionan addition 50 ml of methylene chloride
  3. additionwas added
  4. stirringAfter stirring overnight at ambient temperature
  5. filtrationthe product was collected by filtration (13.5 g, m.p. 196°-199° C.)
  6. customA 6.0 g sample was recrystallized from isopropanol

Sources & evidence

ORD record
ord-ae1dadd083204312b259b840f3cd45b5
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05068231

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes