Cesium carbonate → 6-Chloro-3-[4-(4-chlorophenoxy)-2-propylphenyl]-5-methoxy-1,2-benzisoxazole

HRID 1172828Notes

Reaction equation

HRID 1172828 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([Cl:24])=[CH:18][C:17]=3F)=[N:14]/[OH:15])=[C:9]([CH2:26][CH2:27][CH3:28])[CH:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:24][C:19]1[C:20]([O:22][CH3:23])=[CH:21][C:16]2[C:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][C:5]4[CH:29]=[CH:30][C:2]([Cl:1])=[CH:3][CH:4]=4)=[CH:8][C:9]=3[CH2:26][CH2:27][CH3:28])=[N:14][O:15][C:17]=2[CH:18]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 87541464(NZ)-N-[(4-chloro-2-fluoro-5-methoxyphenyl)-[4-(4-chlorophenoxy)-2-propylphenyl]methylidene]hydroxylamine

Product 1

HCID 686921166-Chloro-3-[4-(4-chlorophenoxy)-2-propylphenyl]-5-methoxy-1,2-benzisoxazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the oxime from Step 4 (1.2 g, 2.7 mmol) and cesium carbonate (1.7 g, 5.4 mmol) in DMF (20 mL) was stirred at 80° C. for 18 h. The reaction was diluted with ethyl acetate and washed with water. The crude product was purified by chromatography on silica gel to give the title product.

Workup

  1. washwashed with water
  2. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-aba7241ea3054d88bafb5dc525a7eefb
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

Loading…