Dimethylformamide → HCID 18426849, compound

HRID 1281138Notes

Reaction equation

HRID 1281138 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([Cl:16])[C:13]([Cl:17])=[CH:12][C:10]=3[N:11]=2)=[CH:5][CH:6]=1.[Na].C([Li])CCC.CN(C)[CH:26]=[O:27]>O1CCCC1.O>[CH:26]([C:2]1[S:3][C:4]([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([Cl:16])[C:13]([Cl:17])=[CH:12][C:10]=3[N:11]=2)=[CH:5][CH:6]=1)=[O:27]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 5360545SodiumHCID 18426820HCID 18426820, compoundHCID 178418339Butyllithium

Product 1

HCID 18426849HCID 18426849, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(2-bromothiophen-5-yl)-5,6-dichlorobenzimidazole (100 mg, 0.287 mmol) in tetrahydrofuran (6 mL) was added sodium hydryde (60% oil dispersion; 14 mg, 0.35 mmol) at 0° C. under nitrogen atmosphere. After cooling to −78° C., n-butyllithium (1.6 mol/L in hexane; 0.36 mL, 0.57 mmol), dimethylformamide (0.085 mL, 1.1 mmol) were added, and the mixture was stirred for 10 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (19:1 to 9:1 chloroform/acetonitrle) to afford 2-(2-formylthiophen-5-yl)-5,6-dichlorobenzimidazole (36 mg, 42%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (19:1 to 9:1 chloroform/acetonitrle)

Sources & evidence

ORD record
ord-34e9119adb3a4e99b267fa235584b935
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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