Hydrochloric Acid → Phenyl 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate

HRID 622181

Reaction equation

HRID 622181 reaction equation
Cl[S:2]([C:5]1[C:13]2[C:9](=[N:10][O:11][N:12]=2)[C:8]([F:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1.Cl>C1C=CC=CC=1.C(Cl)(Cl)Cl>[F:14][C:8]1[C:9]2=[N:10][O:11][N:12]=[C:13]2[C:5]([S:2]([O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 1049PyridineHCID 42069504-(Chlorosulfonyl)-7-fluoro-2,1,3-benzoxadiazole

Product 1

HCID 21293920Phenyl 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6212ChloroformSolvent

Procedure

1.0 g of the compound obtained in Example 1 and 1 g of phenol were dissolved in 5 ml of benzene. Next, after dripping in a chilled mixed solution of 5 ml of benzene and 1 ml of pyridine, the solution was allowed to react for 4 hours at room temperature. After dripping in 50 ml of chilled 10% hydrochloric acid, the solution was extracted with benzene, water washed, and then dried with magnesium sulfate and reduced pressure concentrated. The remaining solid was subjected to chloroform mobile phase; silica gel column chromatography (2 cm ×60 cm) to prepare 2 ml fractions. These were then subjected to thin layer chromatography (silica gel, chloroform) and the fractions with an Rf range in the vicinity of 0.73 were collected. After reduced pressure condensation, the substance was recrystallized using n-hexane. The resulting 0.4 g of white needle shaped crystals had a melting point of between 120° to 121° C.

Workup

  1. customto react for 4 hours at room temperature
  2. extractionthe solution was extracted with benzene, water
  3. washwashed
  4. dry with materialdried with magnesium sulfate and reduced pressure
  5. concentrationconcentrated
  6. customsilica gel column chromatography (2 cm ×60 cm) to prepare 2 ml fractions
  7. customthe fractions with an Rf range in the vicinity of 0.73 were collected
  8. customAfter reduced pressure condensation
  9. customthe substance was recrystallized
  10. customof between 120° to 121° C.

Sources & evidence

ORD record
ord-de05366c141849d8bdd1eee5011e1b58
Source dataset
uspto-grants-1988_09
Patent number
US04769467

Linked notes

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