Thionyl Chloride → methylallyl 6-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazole-1-acetate

HRID 2293735Notes

Reaction equation

HRID 2293735 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])[C:13]=3[CH:22]=2)[CH:5]=[C:4]([F:23])[C:3]=1[C:24]([F:27])([F:26])[F:25].S(Cl)(Cl)=O>CN(C)C=O.C(Cl)Cl.C(#N)C.C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([CH:17]([CH3:21])[C:18]([O:20][CH2:7][CH:2]=[CH:3][CH3:4])=[O:19])[C:13]=3[CH:22]=2)[CH:5]=[C:4]([F:23])[C:3]=1[C:24]([F:27])([F:26])[F:25]

Participants

7

Reactant 2

HCID 24386Thionyl ChlorideHCID 867479436-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazole-1-acetic acid

Product 1

HCID 86747951methylallyl 6-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazole-1-acetate

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-[(2-chloro-α,α,α,6-tetraflouro-p-tolyl)oxy]-α-methyl-1H-benzotriazole-1-acetic acid, thionyl chloride (0.8 ml, 0.011 mole), and 2 drops of dimethylformamide in methylene chloride is heated at reflux temperature for 2 hours, cooled and concentrated in vacuo to give a residue which is re-evaporated four times with toluene at 60° . The resultant residue is treated with 2-methylallyl alcohol and pyridine, shaken until reaction is complete by infrared spectral analysis and concentrated in vacuo to give a residue. The thus-obtained residue is dissolved in 1% acetonitrile in carbon tetrachloride and filtered through a pad of silica. The filtrate is concentrated in vacuo to give a solid residue. The solid residue is recrystallized from warm heptane to afford the title compound as a white solid, mp 71°-74° C., identified by elemental and NMR analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto give a residue which
  6. customis re-evaporated four times with toluene at 60°
  7. additionThe resultant residue is treated with 2-methylallyl alcohol and pyridine
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. filtrationfiltered through a pad of silica
  11. concentrationThe filtrate is concentrated in vacuo
  12. customto give a solid residue
  13. customThe solid residue is recrystallized
  14. temperaturefrom warm heptane

Sources & evidence

ORD record
ord-10ea1722e75c408ab6f244afd444d510
Source dataset
uspto-grants-1997_11
Patent number
US05686617

Reaction notes

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