Nitrogen → HCID 14012483, compound

HRID 652853Notes

Reaction equation

HRID 652853 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[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[F:14].N#N>CN(C=O)C>[Cl:21][C:20]1[C:4]2[O:16][N:15]=[C:6]([C:7]3[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=3[F:14])[C:5]=2[CH:17]=[CH:18][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 947NitrogenHCID 24758Sodium hydrideHCID 86741603HCID 86741603, compound

Product 1

HCID 14012483HCID 14012483, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

To a mixture of 5 g of NaH in 200 ml of DMF, 48 g of 2,3-dichloro-4-methoxy-2',6'-difluorobenzophenone oxime in 250 ml of DMF is added dropwise in an atmosphere of N2 while the temperature is maintained at approximately 40° C. After the addition, the mixture is stirred 30 minutes and poured into ice water. A crude product, which is a mixture of isomers, is filtered off and chromatographed on silica gel with CHCl3 as eluant to yield 7-chloro-3-(2,6-difluorophenyl)-6-methoxy-1,2-benzisoxazole which is recrystallized from toluene for analysis, mp 175°-179° C.

Workup

  1. additionAfter the addition
  2. additiona mixture of isomers
  3. filtrationis filtered off
  4. customchromatographed on silica gel with CHCl3 as eluant

Sources & evidence

ORD record
ord-1810db153e324f4498cb3f03c927d5eb
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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