Water → Ethyl-{[7-chloro-3-(2,3-dimethylphenyl)-1,2-benzisoxazol-6-yl]oxy}acetate

HRID 568640Notes

Reaction equation

Cl[C:2]1[C:18]([Cl:19])=[C:17]([OH:20])[CH:16]=[CH:15][C:3]=1[C:4](=[N:13][OH:14])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[CH3:12].[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][O:20][C:17]1[CH:16]=[CH:15][C:3]2[C:4]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=3[CH3:12])=[N:13][O:14][C:2]=2[C:18]=1[Cl:19])[CH3:29]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 5 g of 2,3-dichloro-4-hydroxy-2',3'-dimethylbenzophenone oxime in 70 ml of DMF, 0.96 g of NaH is added. The internal temperature is held between 95°-120° C. for seven hours, then the mixture is heated at 130° C. for 1.5 hours. The reaction mixture is cooled and 2.94 g of ethyl bromoacetate is added dropwise. The mixture is stirred one hour and water is added dropwise. The product which forms is filtered off and recrystallized from 95% ethanol to yield ethyl-{[7-chloro-3-(2,3-dimethylphenyl)-1,2-benzisoxazol-6-yl]oxy}acetate, mp 89°-91° C.

Workup

temperatureThe reaction mixture is cooled
filtrationThe product which forms is filtered off
customrecrystallized from 95% ethanol

Sources & evidence

ORD record: ord-1c2a97df096a45b3bf9eeb13bf26a144
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04728662

Reaction notes

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