Hydrochloric Acid → HCID 13505093, compound

HRID 746082Notes

Reaction equation

HRID 746082 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:29]=[CH:28][C:15]([O:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([N+:24]([O-])=O)=[CH:19][C:18]=3[Cl:27])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCOCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[CH:29]=[CH:28][C:15]([O:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([NH2:24])=[CH:19][C:18]=3[Cl:27])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13505092HCID 13505092, compound

Product 1

HCID 13505093HCID 13505093, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 100 mL flask equipped with condenser, stirrer, under nitrogen atmosphere was added 26.9 g. (0.11 mol) of stannous chloride, 23.9 mL of concentrated hydrochloric acid, and 17.9 mL of p-dioxane. The resulting mixture was warmed to 40° to obtain a homogeneous solution. To the above solution was added 16.6 g (0.036 mol) of 4-(4-[4-chlorophenylsulfonyl]phenoxy)-3,5-dichloronitrobenzene. The mixture was heated to reflux for 0.5 hour, cooled, and poured into chilled aqueous sodium hydroxide (pH 14). This mixture was extracted twice with methylene chloride. The combined organic layer was washed successively with aqueous sodium hydroxide, water, and brine. It was then dried over sodium sulfate and was concentrated to give 14.2 g (0.033 mol) of a white solid; mp 186°-187° C.

Workup

  1. customTo a 100 mL flask equipped with condenser, stirrer, under nitrogen atmosphere
  2. additionwas added 26.9 g
  3. temperatureThe resulting mixture was warmed to 40°
  4. customto obtain a homogeneous solution
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 0.5 hour
  7. temperaturecooled
  8. additionpoured
  9. extractionThis mixture was extracted twice with methylene chloride
  10. washThe combined organic layer was washed successively with aqueous sodium hydroxide, water, and brine
  11. dry with materialIt was then dried over sodium sulfate
  12. concentrationwas concentrated

Sources & evidence

ORD record
ord-0c8be5020e0d449a80e7672690eda1c5
Source dataset
uspto-grants-1986_07
Patent number
US04602109

Reaction notes

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