Hydrochloric Acid → HCID 178518988, compound

HRID 1901592Notes

Reaction equation

HRID 1901592 reaction equation
[F:1][C:2]1[CH:11]=[C:6]([C:7]([NH:9]O)=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.Cl>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:12][N:9]=[C:7]([OH:8])[C:6]=2[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 12365889HCID 12365889, compound

Product 1

HCID 178518988HCID 178518988, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2.44 g of 5-fluorosalicylhydroxamic acid in 22 ml of tetrahydrofuran is added 1.83 g of thionyl chloride at 10° C., and they are subjected to reaction at 20°-25° C. for one hour. Subsequently, at 10°-15° C., 4.67 g of triethylamine is dropped over 30 minutes, and thereafter, reaction is effected at 20°-25° C. for one hour. To the reaction mixture is added 200 ml of water, and the pH is adjusted to 3 with 2N hydrochloric acid. The crystals precipitated are collected by filtration to obtain 1.32 g of colorless, crystalline 5-fluoro-3-hydroxy-1,2-benzoisoxazole having a melting point of 201°-203° C.

Workup

  1. customthey are subjected to reaction at 20°-25° C. for one hour
  2. customreaction
  3. customThe crystals precipitated
  4. filtrationare collected by filtration

Sources & evidence

ORD record
ord-4ac0d1701a734f568cdc3ad05057c5b6
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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