Water → HCID 178521825, compound

HRID 2263039Notes

Reaction equation

HRID 2263039 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19].O>O1CCCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:18](=[O:19])[O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 178507353HCID 178507353, compound

Product 1

HCID 178521825HCID 178521825, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-benzimidazol-5-amine (1.00 g, 7.51 mmol) and pyridine (0.73 ml, 9.01 mmol) in tetrahydrofuran (25 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.25 ml, 9.01 mmol), and the mixture was stirred at room temperature for 1.5 hour. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 1.49 g (64.4%) of the desired product as a solid was separated by filtration.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue, and 1.49 g (64.4%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-d5ba8b1c5f304d0bb8f6a2270e0cb62c
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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