Water → HCID 14012509, compound

HRID 568687Notes

Reaction equation

HRID 568687 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)=[N:11][OH:12].[H-].[Na+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C=O)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][O:9][C:6]1[CH:5]=[CH:4][C:3]2[C:10]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:2]=2[C:7]=1[Cl:8])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 136477366HCID 136477366, compound

Product 1

HCID 14012509HCID 14012509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3 g of (2,3-dichloro-4-hydroxyphenyl)(1-naphthyl)methanone oxime in 25 ml of DMF, 0.54 g of NaH is added under N2. The mixture is heated to an internal temperature of 100° C. for one hour and 20 minutes. The reaction mixture is cooled to room temperature and 1.65 g of ethyl bromoacetate is added dropwise. The mixture is stirred for 18 hours, water is added and the product is extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried over Na2SO4 and evaporated to give ethyl{[7-chloro-3-(1-napthyl)-1,2-benzisoxazol-6-yl]oxy}acetate, mp 75°-85° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionthe product is extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-57d6e42d88204f63bc97a21b01f6f251
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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