Sulfuryl chloride → HCID 19754664, compound

HRID 1588797Notes

Reaction equation

HRID 1588797 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH2:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[CH:14]1.S(Cl)([Cl:27])(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH2:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]1[Cl:27]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19754602HCID 19754602, compound

Product 1

HCID 19754664HCID 19754664, compoundYield 31.62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.0 g (15.15 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-amino-4-trifluoromethylsulfenylimidazole in 100 ml of methylene chloride was added 1.70 ml (18.18 mmole) of sulfuryl chloride at 0° C. The resulting mixture was stirred at RT for 5 days under a nitrogen atmosphere. The mixture was quenched with water, then partitioned between methylene chloride and aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by column chromatography using 20% ethyl acetate in hexane to give 1.9 g (31.62% yield) of the desired product, mp 172.5° C.

Workup

  1. customThe mixture was quenched with water
  2. custompartitioned between methylene chloride and aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c6351a817e944cedbd73241e3fc5a4fd
Source dataset
uspto-grants-1993_06
Patent number
US05223525

Reaction notes

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