Sodium Bicarbonate → HCID 58498007, compound

HRID 1505255Notes

Reaction equation

HRID 1505255 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[C:12](/Cl)=[N:13]/[OH:14])=[C:6]2[C:10]=1[O:9][C:8]([CH3:11])=[N:7]2.[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([C:25]([F:28])([F:27])[F:26])=[CH2:24])[CH:20]=[C:19]([Cl:29])[CH:18]=1.C(=O)([O-])O.[Na+]>CC(O)C>[Br:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])=[N:7][C:6]=2[C:5]([C:12]2[CH2:24][C:23]([C:21]3[CH:20]=[C:19]([Cl:29])[CH:18]=[C:17]([Cl:16])[CH:22]=3)([C:25]([F:26])([F:28])[F:27])[O:14][N:13]=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 58497920HCID 58497920, compound

Product 1

HCID 58498007HCID 58498007, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 7-bromo-N-hydroxy-2-methyl-benzo[d]oxazole-4-carbimidoyl chloride (Example 6.8) (3.63 g) in 2-propanol (100 ml) was added 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (preparation described in, for example, EP 1,731,512) (3.43 g) and sodium hydrogen carbonate (1.44 g). The reaction mixture was stirred at 65° C. for 16 hours. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (eluent: 2-25% v/v ethyl acetate in heptane) to give 7-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-2-methyl-benzo[d]oxazole (3.7 g). 1H-NMR (400 MHz, CDCl3): 7.71-7.42 (m, 5H), 4.50 (d, 1H), 4.06 (d, 1H), 2.73 (s, 3H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel (eluent: 2-25% v/v ethyl acetate in heptane)

Sources & evidence

ORD record
ord-77e212589ef14944aed3981c86d78696
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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