Diisopropylethylamine → Methyl 2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-4-carboxylate

HRID 1698603Notes

Reaction equation

HRID 1698603 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(C(C)C)CC)(C)C.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[O:29]=[C:27]1[NH:12][C:11]2[C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[NH:1]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 67273073Methyl 2,3-diamino-4-(trifluoromethyl)benzoate

Product 1

HCID 67272796Methyl 2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirring solution of methyl 2,3-diamino-4-(trifluoromethyl)benzoate (5.10 g, 0.022 mol) and diisopropylethylamine (6.26 g, 0.048 mol) in toluene (50 ml) was added a solution of triphosgene (2.58 g, 0.0087 mol) in toluene (20 ml) dropwise and stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo. The residue was diluted with 1N hydrochloric acid and extracted with ethyl acetate and tetrahydrofuran. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. A solution of 50% diisopropylether/n-hexane was added to the residue and white precipitates were filtered, washed with same solvent to give 5.00 g (0.019 mol 87%) of the title as a white powder

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with 1N hydrochloric acid
  3. extractionextracted with ethyl acetate and tetrahydrofuran
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additionA solution of 50% diisopropylether/n-hexane was added to the residue
  8. customwhite precipitates
  9. filtrationwere filtered
  10. washwashed with same solvent
  11. customto give 5.00 g (0.019 mol 87%) of the title as a white powder

Sources & evidence

ORD record
ord-6a4977369f4d4c60b5f2471fb5cd60b9
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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