Water → HCID 14012509, compound

HRID 652916Notes

Reaction equation

HRID 652916 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-d448f20349684486844ecd4b9249c128
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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