2,6-Dichlorobenzaldehyde → 2-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1360713Notes

Reaction equation

HRID 1360713 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=1>CS(C)=O.CCOC(C)=O>[CH3:11][O:12][C:13]([C:14]1[CH:19]=[CH:18][C:17]2[N:20]=[C:4]([C:3]3[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=3[Cl:10])[NH:21][C:16]=2[CH:15]=1)=[O:22]

Participants

5

Reactant 2

HCID 67372,6-DichlorobenzaldehydeHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 669663062-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Slowly add a solution of FeCl3 (1.46 g, 9.02 mmol) in DMSO (10 mL) to a stirring solution of 2,6-dichloro-benzaldehyde (5.27 g, 30.1 mmol) and 3,4-diamino-benzoic acid methyl ester (5.00 g, 30.1 mmol) in DMSO (90 mL). Allow the reaction to stir open to the air for 17 hr. Add additional FeCl3 (0.73 g, 4.51 mmol). Stir for an additional 24 hr. Dilute with EtOAc (600 mL) and extract with water (3×50 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Triturate the residue with DCM to afford the desired product as a light tan solid: 1H NMR (400 MHz, MeOD) δ ppm 3.96 (s, 3H) 7.55-7.63 (m, 3H) 7.71 (d, J=8.21 Hz, 1H) 8.04 (dd, J=8.53, 1.58 Hz, 1H) 8.37 (br. s., 1H); (M+H)+ 320.9.

Workup

  1. customthe reaction
  2. stirringStir for an additional 24 hr
  3. extractionextract with water (3×50 mL)
  4. dry with materialDry the organic phase over Na2SO4
  5. customevaporate the solvent
  6. customTriturate the residue with DCM

Sources & evidence

ORD record
ord-4ad27aeb9ff24ff29f21f4933a9e6f58
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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