Water → HCID 14012477, compound

HRID 652843Notes

Reaction equation

HRID 652843 reaction equation
Cl[C:2]1[C:16]([Cl:17])=[C:15]([OH:18])[CH:14]=[CH:13][C:3]=1[C:4](=[N:11][OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:18][C:15]1[CH:14]=[CH:13][C:3]2[C:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[N:11][O:12][C:2]=2[C:16]=1[Cl:17])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride2×HCID 136393678HCID 136393678, compound

Product 1

HCID 14012477HCID 14012477, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2,3-dichloro-4-hydroxybenzophenone oxime and 2.6 g of sodium hydride in 50 ml of dimethylformamide and 50 ml of toluene is heated to 118° C. and maintained at this temperature for 50 minutes. Thereafter, the reaction is permitted to cool prior to the dropwise addition of 7.9 g of ethyl bromoacetate in 50 ml of dimethylformamide. After the addition is complete the reaction mixture is stirred at ambient temperature for 40 minutes. To the well stirred mixture water is added dropwise to decompose any excess sodium hydride. The toluene is evaporated under vacuum and the resulting precipitate is collected by filtration and then rinsed with ether to yield the product ethyl[(7-chloro-3-phenyl-1,2-benzisoxazol-6-yl)oxy]acetate having a melting point of 130° to 132° C.

Workup

  1. temperaturemaintained at this temperature for 50 minutes
  2. temperatureto cool
  3. additionAfter the addition
  4. additionis added dropwise
  5. customThe toluene is evaporated under vacuum
  6. filtrationthe resulting precipitate is collected by filtration
  7. washrinsed with ether

Sources & evidence

ORD record
ord-056150d0a5e74c4f9828c5cef46aaf68
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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