Water → HCID 13015713, compound

HRID 568610Notes

Reaction equation

HRID 568610 reaction equation
Cl[C:2]1[C:17]([Cl:18])=[C:16]([OH:19])[CH:15]=[CH:14][C:3]=1[C:4](=[N:12][OH:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C)C=O.C1C=CC=CC=1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:19][C:16]1[CH:15]=[CH:14][C:3]2[C:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[F:11])=[N:12][O:13][C:2]=2[C:17]=1[Cl:18])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride2×HCID 136359213HCID 136359213, compound

Product 1

HCID 13015713HCID 13015713, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 18.4 g of 2,3-dichloro-4-hydroxy-2'-fluorobenzophenone oxime and 3.6 g of sodium hydride in 120 ml of dimethylformamide and 120 ml of benzene is maintained at a temperature of from 80°-85° C. for 3 hours. Thereafter, the mixture is permitted to reach ambient temperature after which a solution of 11.0 g of ethyl bromoacetate in 20 ml of dimethylformamide is added dropwise. After the addition is complete, the mixture is stirred for 30 minutes and then water is added to decompose any excess sodium hydride. The mixture is extracted with ethyl acetate and the combined extracts are dried and evaporated to dryness leaving a solid residue. The residue is recrystallized several times from 95% ethyl alcohol to yield the pure product ethyl{[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetat having a melting point of 102° to 104° C.

Workup

  1. customto reach ambient temperature
  2. additionis added dropwise
  3. additionAfter the addition
  4. extractionThe mixture is extracted with ethyl acetate
  5. customthe combined extracts are dried
  6. customevaporated to dryness
  7. customleaving a solid residue
  8. customThe residue is recrystallized several times from 95% ethyl alcohol

Sources & evidence

ORD record
ord-04664d72192e4f258f3c1d124b08ec71
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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