3,5-Diamino-2-methylbenzoic acid → HCID 66965685, compound

HRID 1514899Notes

Reaction equation

HRID 1514899 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH:4]=O.[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>CS(C)=O>[CH3:14][O:15][C:16]([C:17]1[CH:22]=[CH:21][C:20]2[N:23]=[C:4]([C:3]3[C:6]([C:10]([F:13])([F:12])[F:11])=[CH:7][CH:8]=[CH:9][C:2]=3[Cl:1])[NH:24][C:19]=2[CH:18]=1)=[O:25]

Participants

5

Reactant 3

HCID 1355243,5-Diamino-2-methylbenzoic acidHCID 2733225Ytterbium triflateHCID 177506792-Chloro-6-(trifluoromethyl)benzaldehyde

Product 1

HCID 66965685HCID 66965685, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2-chloro-6-trifluoromethylbenzaldehyde (270 mg, 1.3 mmol) and 3,4-diaminobenzoic acid methyl ester (216 mg, 1.3 mmol) in DMSO (10 mL) was added Yb(OTf)3 (161 mg, 0.26 mmol) and the solution was stirred at ambient temperature overnight. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure to give 2-(2-chloro-6-trifluoromethylphenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester as a red oil. This was used directly in the next step.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de77a89c0eb44baca6dedd2477fba468
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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