Sodium Bicarbonate → 5-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(3,3,3-trifluoropropyl)benzimidazole

HRID 74319Notes

Reaction equation

HRID 74319 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:17][CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:14]([CH:16]=3)[NH2:15])=[N:7][C:6]=2[CH:24]=1.Cl.[C:26](=N)(OCC)[CH3:27].C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[N:17]([CH2:18][CH2:19][C:20]([F:21])([F:23])[F:22])[C:26]([CH3:27])=[N:15][C:14]=4[CH:16]=3)=[N:7][C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 674982645-Chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 498215355-(5-Chlorobenzoxazol-2-yl)-2-methyl-1-(3,3,3-trifluoropropyl)benzimidazoleYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole (see Working Example 138-1) (200 mg, 0.562 mmol) in ethanol (5 mL) was added ethyl acetimidate hydrochloride (104 mg, 0.843 mmol), and this was heated to reflux for 5 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude crystals that were washed with diethyl ether to yield the title compound (170 mg, 80% yield) as light green crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 5 hours
  3. extractionthis was extracted with chloroform
  4. customThe organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude crystals that
  9. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-46ab008a7a4940b8b5c4581815ee73db
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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