HCID 11265881, compound → HCID 86703255, compound

HRID 337346Notes

Reaction equation

HRID 337346 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[NH2:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1>N([O-])=O.[Na+].O.Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N:19]2[C:17]([CH3:16])=[CH:12][C:13]([CH3:14])=[N:19]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 11265881HCID 11265881, compound

Product 1

HCID 86703255HCID 86703255, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 23668193Sodium NitriteSolvent

Procedure

To 453 mg of 2-amino-5-methylphenyl 4-methylbenzene sulfonate was added 1.6 ml of 5N-hydrochloric acid, and a solution in which 146 mg of sodium nitrite was dissolved in 1 ml of water was added dropwise at 0° C., and stirred for 30 minutes. Then, a solution in which 736 mg of stannous chloride was dissolved in 0.8 ml of 5N-hydrochloric acid was added dropwise at 0° C. and stirred for 1 hour. The solvent was distilled off under reduced pressure, 3.2 ml of ethanol and 167 μl of acetyl acetone were added and heated at reflux for 2 hours. To the reaction mixture was added 50 ml of water, neutralized with a saturated sodium bicarbonate solution, and extracted with 80 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using silica gel column chromatography (hexane:ethyl acetate=2:1) to yield 199.6 mg of the title compound.

Workup

  1. additionwas added dropwise at 0° C.
  2. additionwas added dropwise at 0° C.
  3. stirringstirred for 1 hour
  4. distillationThe solvent was distilled off under reduced pressure, 3.2 ml of ethanol and 167 μl of acetyl acetone
  5. additionwere added
  6. temperatureheated
  7. temperatureat reflux for 2 hours
  8. additionTo the reaction mixture was added 50 ml of water
  9. extractionextracted with 80 ml of ethyl acetate
  10. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. custompurified

Sources & evidence

ORD record
ord-03c2191db1c74c1fb7a384d9513a9bbf
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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