Sodium Sulfate → 7-Chloro-6-methoxy-1,2-benzoxazole

HRID 568676Notes

Reaction equation

HRID 568676 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[NH2:13]OS(O)(=O)=O.[O-]S([O-])(=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]1[C:3]2[O:12][N:13]=[CH:5][C:4]=2[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 133437063-Chloro-4-methoxysalicylaldehyde

Product 1

HCID 140125047-Chloro-6-methoxy-1,2-benzoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-chloro-2-hydroxy-4-methoxybenzaldehyde (1.48 g) is suspended in 15 ml of H2O and hydroxylamine-O-sulfonic acid (1.08 g) is added, along with 0.1 g of Na2SO4. After three hours an additional 15 ml of H2O is added. After a total of four hours the reaction mixture is treated with 8% NaHCO3 solution and then extracted into ether. Evaporation and trituration with hexane gives a solid product. Recrystallization from toluene/hexane gives 7-chloro-6-methoxy-1,2-benzisoxazole, mp 115°-118° C.

Workup

  1. extractionextracted into ether
  2. customEvaporation and trituration with hexane
  3. customgives a solid product
  4. customRecrystallization from toluene/hexane

Sources & evidence

ORD record
ord-a654858dcc9a43cc852e2cc58e154010
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

Loading…