Sodium Hydroxide → HCID 22176571, compound

HRID 1797196Notes

Reaction equation

HRID 1797196 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([N+]([O-])=O)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[H+].[B-](F)(F)(F)F.N([O-])=[O:28].[Na+].[OH-].[Na+]>O>[OH:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([OH:28])=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 28118Tetrafluoroboric acidHCID 22176567HCID 22176567, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22176571HCID 22176571, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Into a 50 mL-3 neck flask fitted with a stirrer and thermometer was placed 1.0 gm. Of [2-(4-aminophenyl)-2-hydroxypropyl][(methylethyl)sulfonyl]amine (prepared in example 19) and 4.06 gm of 48% HBF4 in H2O (20 mL) at 0° C. The reaction was then stirred at this temperature for 30 minutes. 0.26 gm of sodium nitrite was then added portion wise to the mixture and stirring at this temperature continued for an additional 30 minutes. The reaction was then slowly heated to 70° C. and stirred at this temperature for 3 hours. The mixture was cooled to room temperature and the solution was taken to pH 12 with 1 N NaOH and the solution was filtered. The filtrate was the taken to pH 3.0 with 1 N HCl and the desired product was extracted into ethyl acetate. The organic layer was dried over Na2SO4, and concentrated under reduced vacuum to yield 1.20 gm of a dark oil. This two spot material was purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 9:1. Collection of the bottom spot provided the intermediate title compound (200 mg, 20%) as a slowly crystallizing oil. Ion spray M.S. 272.4 (M*−1).

Workup

  1. customInto a 50 mL-3 neck flask fitted with a stirrer
  2. customat 0° C
  3. stirringstirring at this temperature
  4. waitcontinued for an additional 30 minutes
  5. stirringstirred at this temperature for 3 hours
  6. temperatureThe mixture was cooled to room temperature
  7. filtrationthe solution was filtered
  8. extractionthe desired product was extracted into ethyl acetate
  9. dry with materialThe organic layer was dried over Na2SO4
  10. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-11a1a9217ec0474db4a72cd6c67fe202
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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