Sodium hydride → HCID 14012515, compound

HRID 568692Notes

Reaction equation

HRID 568692 reaction equation
[H-].[Na+].Cl[C:4]1[C:20]([Cl:21])=[C:19]([O:22][CH3:23])[CH:18]=[CH:17][C:5]=1[C:6](=[N:15][OH:16])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[F:14]>CN(C=O)C>[Cl:21][C:20]1[C:4]2[O:16][N:15]=[C:6]([C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=3[F:14])[C:5]=2[CH:17]=[CH:18][C:19]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86741617HCID 86741617, compound

Product 1

HCID 14012515HCID 14012515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 2.24 g of NaH in 100 ml DMF, 21.75 g of 2,3-dichloro-4-methoxy-4'-chloro-2'-fluorobenzophenone oxime in 100 ml of DMF is added dropwise. After addition the mixture is stirred one hour and the reaction mixture poured into ice water. A product which precipitates is filtered and dried giving a mixture of isomers which is chromatographed on silica gel with 50% hexane and 50% toluene as eluant to yield 7-chloro-3-(4-chloro-2-fluorophenyl)-6-methoxy-1,2-benzisoxazole, mp 193°-194° C.

Workup

  1. additionis added dropwise
  2. additionAfter addition the mixture
  3. customA product which precipitates
  4. filtrationis filtered
  5. customdried
  6. customgiving
  7. additiona mixture of isomers which
  8. customis chromatographed on silica gel with 50% hexane and 50% toluene as eluant

Sources & evidence

ORD record
ord-705d027f9d7c458dbfff2889dbc6b2a5
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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