Hydrochloric Acid → HCID 68826189, compound

HRID 984708Notes

Reaction equation

HRID 984708 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH3:16][NH2:17].[OH-].[K+].Cl>>[CH3:16][NH:17][S:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)(=[O:14])=[O:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 14797Potassium HydroxideHCID 144577416-Bromonaphthalene-2-sulfonyl chloride

Product 1

HCID 68826189HCID 68826189, compound

Procedure

6-Bromonaphthalene-2-sulfonyl chloride (576 mg) was added portionwise to 40% methylamine solution (5 ml, WAKO), added with 3.6 N aqueous potassium hydroxide (5 ml), stirred at room temperature, then heated to 60° C. and further stirred for 3 hours. The reaction mixture was cooled to room temperature, then added with 2 N hydrochloric acid (15 ml) and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (Intermediate 30, 484 mg).

Workup

  1. temperatureheated to 60° C.
  2. stirringfurther stirred for 3 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-da22809e91be45d081a06c824c766dd9
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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