Sodium hydride → HCID 14012515, compound

HRID 652921Notes

Reaction equation

HRID 652921 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-cb80c98f303646c8aa9a9dac7df1d886
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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