Benzaldehyde → HCID 69135079, compound

HRID 969514Notes

Reaction equation

HRID 969514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1.C([Mg]Br)=C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:23]=[CH2:24])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 45789404HCID 45789404, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 69135079HCID 69135079, compoundYield 747.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

6.4 g (26.7 mmol) 6-bromo-1,2-dimethyl-1H-benzimidazol-4-ylamine, 8.5 g (80 mmol) benzaldehyde and 0.3 g p-toluenesulphonic acid monohydrate in 80 ml toluene were refluxed on a Dean-Stark-trap. After complete reaction, the mixture was evaporated to one third of its volume and diluted with 50 ml tetrahydrofuran. The mixture was cooled to 0° C. and 80 ml (80 mmol) vinylmagnesiumbromide (1M solution in tetrahydrofuran) were added during 45 min. After 30 min., the reaction mixture was hydrolyzed with saturated ammonium chloride solution, diluted with water and extracted with ethyl acetate. The organic phase was separated, washed with water, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=7:3). Crystallization from diisopropyl ether afforded 4.2 g (44%) of the title compound as a colourless solid. m.p. 137-139° C.

Workup

  1. customAfter complete reaction
  2. customthe mixture was evaporated to one third of its volume
  3. additiondiluted with 50 ml tetrahydrofuran
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=7:3)
  10. customCrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-4880544e374f44ef8327b27d4b4a37ec
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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