Sodium Carbonate → HCID 178506264, compound

HRID 2199503Notes

Reaction equation

HRID 2199503 reaction equation
Cl[C:2]1[C:14]([Cl:15])=[CH:13][C:5]2[NH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[N:8][C:4]=2[CH:3]=1.O1CCOCC1.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[Cl:29].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:15][C:14]1[C:2]([C:26]2[CH:25]=[CH:24][C:23]([Cl:22])=[C:28]([Cl:29])[CH:27]=2)=[CH:3][C:4]2[NH:8][C:7]([C:9]([F:12])([F:11])[F:10])=[N:6][C:5]=2[CH:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 168595,6-Dichloro-2-trifluoromethylbenzimidazoleHCID 312751,4-DioxaneHCID 27343303,4-Dichlorobenzeneboronic acid

Product 1

HCID 178506264HCID 178506264, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound number 258 (i.e., 6-chloro-5-(3,4-dichlorophenyl)-2-trifluoromethylbenzimidazole) was prepared as follows. A 100-mL round-bottom flask was purged and maintained with an inert atmosphere of nitrogen. 5,6-dichloro-2-(trifluoromethyl)-1H-1,3-benzodiazole (200 mg, 0.78 mmol, 1.00 equiv), 1,4-dioxane (30 mL), (3,4-dichlorophenyl)boronic acid (229 mg, 1.20 mmol, 2.00 equiv), sodium carbonate (191 mg), water (8 mL) and Pd(PPh3)4 (34.7 mg) was placed into the flask. The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 82.4 mg (29%) of 6-chloro-5-(3,4-dichlorophenyl)-2-trifluoromethylbenzimidazole as a white solid.

Workup

  1. customA 100-mL round-bottom flask was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 82.4 mg (29%) of 6-chloro-5-(3,4-dichlorophenyl)-2-trifluoromethylbenzimidazole as a white solid

Sources & evidence

ORD record
ord-817ec8c702174c919db82a8ad9292103
Source dataset
uspto-grants-2016_06
Patent number
US09359305B2

Reaction notes

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