Thionyl Chloride → HCID 14990630, compound

HRID 2248326Notes

Reaction equation

HRID 2248326 reaction equation
[CH2:1]([N:5]1[C:9]2[CH:10]=[C:11]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)O)[CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:25])=O>O1CCCC1>[CH2:1]([N:5]1[C:9]2[CH:10]=[C:11]([CH:14]([Cl:25])[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14990599HCID 14990599, compound

Product 1

HCID 14990630HCID 14990630, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6.5 parts of 1-butyl-α-(3-chlorophenyl)-1H-benzotriazole-6-methanol in 45 parts of tetrahydrofuran were added 3.7 parts of thionyl chloride at room temperature. After stirring for 1 hour, the reaction mixture was concentrated. The product was extracted with ethyl acetate. The extract was washed with a diluted sodium hydrogen carbonate solution, dried, filtered and evaporated, yielding 6.2 parts (88.3%) of 1-butyl-6-[chloro(3-chlorophenyl)methyl]-1H-benzotriazole as a residue (int. 73).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionThe product was extracted with ethyl acetate
  3. washThe extract was washed with a diluted sodium hydrogen carbonate solution
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3e0fa10c747642b89cf08f7ab0f182c1
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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