Hydrochloric Acid → HCID 18454316, compound

HRID 1271504Notes

Reaction equation

HRID 1271504 reaction equation
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[N:13]([O-])=O.[Na+].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1>C1COCC1.O>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:13]=[N:9][C:8]2[CH:10]=[CH:11][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[C:20]([CH3:24])[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7934m-ToluidineHCID 796174-(Methylsulfonyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 18454316HCID 18454316, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

For their studies, p-Methylsulfonylaniline (1.42 g, 8.3 mmol) was sequentially treated with HCl (15 ml of a 6M solution, 9 mmol) and sodium nitrite (0.66 g, 9.12 mmol) while the temperature was maintained between 0–5° C. The reagents were allowed to dissolve and the resulting solution was allowed to stir for an about 15 minutes. The resulting diazonium compound was then treated with m-toluidine (0.9 g, 8.4 mmol) in THF, and allowed to stir for about 15 minutes to 1 h. To the resulting red-orange mixture was added sodium acetate NaOAc) (2 g, 2 mmol) or water and allowed to stir for about 16 h. The precipitated orange solid was filtered, sequentially washed with water/ethanol and hexanes, and dried under vacuum and recrystallized from EtOAc/Hexane to give 1.96 g (73.3%) of Compound 3.

Workup

  1. temperaturewas maintained between 0–5° C
  2. dissolutionto dissolve
  3. stirringto stir for about 15 minutes to 1 h
  4. stirringto stir for about 16 h
  5. filtrationThe precipitated orange solid was filtered
  6. washsequentially washed with water/ethanol and hexanes
  7. customdried under vacuum
  8. customrecrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-bf5f5cce6b2e4f6b93805ace516d3ade
Source dataset
uspto-grants-2007_04
Patent number
US07205347B2

Reaction notes

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