1,4-Dioxane → 4-[(1-Amino-9,10-dihydro-4-hydroxy-9,10-dioxo-2-anthracenyl)oxy]benzenesulfonyl fluoride

HRID 962350Notes

Reaction equation

HRID 962350 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O1CCOCC1.[F-:36].[K+]>O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([F:36])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 87461Benzenesulfonyl chloride, 4-[(1-amino-9,10-dihydro-4-hydroxy-9,10-dioxo-2-anthracenyl)oxy]-HCID 522689Potassium Fluoride

Product 1

HCID 190833974-[(1-Amino-9,10-dihydro-4-hydroxy-9,10-dioxo-2-anthracenyl)oxy]benzenesulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-amino-4-hydroxy-2-(4-chlorosulphonylphenoxy)anthraquinone (2 parts) and 1,4-dioxane (25 parts), stirring at ambient temperature, was added a solution of potassium fluoride (0.6 parts) in water (5 parts). The mixture was heated to 60° C. and stirred at this temperature for 20 minutes. After cooling to 0°-5° C., the product was isolated by filtration, washed with water and dried at 50° C. to yield: 1-amino-4-hydroxy-2-(4-fluorosulphonylphenoxy)anthraquinone (1.6 parts). λmax=515.0 nm (CH2Cl2).

Workup

  1. temperatureThe mixture was heated to 60° C.
  2. stirringstirred at this temperature for 20 minutes
  3. temperatureAfter cooling to 0°-5° C.
  4. customthe product was isolated by filtration
  5. washwashed with water
  6. customdried at 50° C. to yield

Sources & evidence

ORD record
ord-18cdd58fa173405d9ecfc18d31e4984e
Source dataset
uspto-grants-1998_06
Patent number
US05759211

Reaction notes

Loading…