Hydrochloric Acid → HCID 10408480, compound

HRID 644391Notes

Reaction equation

HRID 644391 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20]C)=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)(=[O:10])=[O:9])[CH:7]=1.[I-].[Li+].N1C(C)=CC(C)=CC=1C.Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 3691436HCID 3691436, compound

Product 1

HCID 10408480HCID 10408480, compoundYield 45.3%

Procedure

A mixture of the white crystal of 5-Bromo-N-(3,5-dichlorophenyl)-2-methoxybenzenesulfonamide (206 mg, 0.5 mmol), lithium iodide (134 mg, 1 mmol) and 2,4,6-collidine (5 mL) was refluxed for 30 minutes under argon atmosphere. After cooling to room temperature, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was crystallized from n-hexane-ethyl acetate to give the title compound (90 mg, 45.3%) as a white crystal.

Workup

  1. temperaturewas refluxed for 30 minutes under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was crystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-c391bba0ec144ee4aa0e5b3ebbc04b7c
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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