Thionyl Chloride → 5-(Chloromethyl)-1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-1H-tetrazole
Reaction equation
[F:1][S:2]([F:19])([F:18])([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14]O)=[N:12][N:11]=[N:10]2)=[CH:5][CH:4]=1.O=S(Cl)[Cl:22]>C1(C)C=CC=CC=1>[Cl:22][CH2:14][C:13]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([S:2]([F:19])([F:18])([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)[N:10]=[N:11][N:12]=1Participants
4
Procedure
Thionyl chloride (1.72 g, 14.4 mmol) was added to a stirred solution of {1-[4-(pentafluoro-λ6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methanol (Intermediate 44, 3.50 g, 11.6 mmol) in toluene (40 mL), SOCl2 at room temperature. The reaction mixture was stirred for 4 hr at reflux. The reaction mixture was concentrated under vacuum. The residue was diluted with DCM and washed with ice-water, saturated aq NaHCO3 and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluted with 20%-30% EtOAc/pet-ether to give the title compound as a brown gum (3.50 g).
Workup
- temperatureat reflux
- concentrationThe reaction mixture was concentrated under vacuum
- additionThe residue was diluted with DCM
- washwashed with ice-water, saturated aq NaHCO3 and brine solution
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customto give the crude compound
- customThis was purified by column chromatography (100-200 mesh silica gel)
- washeluted with 20%-30% EtOAc/pet-ether
Sources & evidence
- ORD record
- ord-f7aa9686189d4119b57558a68359dcb3
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
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