Water → HCID 66965285, compound

HRID 1514892Notes

Reaction equation

HRID 1514892 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1.[CH3:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:15]=1[CH:16]=O.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].O>CS(C)=O.CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:16]([C:15]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:14]=3[CH3:13])[NH:11][C:6]=2[CH:5]=1)=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 5838412,6-DimethylbenzaldehydeHCID 2733225Ytterbium triflate

Product 1

HCID 66965285HCID 66965285, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-diaminobenzoic acid methyl ester (5.2 g) and 2,6-dimethylbenzaldehyde (4.2 g) in DMSO (50 mL) was added Yb(OTf)3 (3.9 g). The mixture was stirred at room temperature for 18 h. The mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated to give 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester as a red solid; MS (ESI)m/z 281 (M+H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6a05284775848b99b831ff12ca99ff2
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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