Sodium Carbonate → HCID 178506264, compound

HRID 1468093Notes

Reaction equation

HRID 1468093 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-4ca3a08d94e14008a2b8ff73e0d0c505
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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