Sodium Bicarbonate → 4-Bromo-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole

HRID 1505245Notes

Reaction equation

HRID 1505245 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([C:11](Cl)=[N:12][OH:13])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([C:24]([F:27])([F:26])[F:25])=[CH2:23])[CH:19]=[C:18]([Cl:28])[CH:17]=1.C(=O)([O-])O.[Na+]>CC(O)C>[Br:1][C:2]1[C:10]2=[N:9][S:8][N:7]=[C:6]2[C:5]([C:11]2[CH2:23][C:22]([C:20]3[CH:19]=[C:18]([Cl:28])[CH:17]=[C:16]([Cl:15])[CH:21]=3)([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 1363510707-bromo-N-hydroxybenzo[1,2,5]thiadiazole-4-carbimidoyl chloride

Product 1

HCID 584979314-Bromo-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazoleYield 52.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 7-bromo-N-hydroxy-benzo[1,2,5]thiadiazole-4-carbimidoyl chloride (Example 5.5) (10.01 g) in 2-propanol (140 ml) was added 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (preparation described in, for example, EP 1,731,512) (6.87 g) and sodium hydrogen carbonate (5.99 g). The reaction mixture was stirred at 65° C. for 3 hours. The reaction mixture was concentrated and the residue was purified by column chromatography (heptane/ethyl acetate 9:1) to give 4-bromo-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzo[1,2,5]thiadiazole (7.4 g). 1H-NMR (DMSO-d6, 400 MHz): 8.17-7.53 (m, 5H), 4.70 (d, 1H), 4.49 (d, 1H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography (heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-14b8f13d67f74e118c9a8eacff345559
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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