Water → 2,2,2-Trichloroethyl (1-methyl-1H-benzimidazol-2-yl)carbamate

HRID 2262937

Reaction equation

HRID 2262937 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH2:11].N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].O>O1CCCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH:11][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 741872-Amino-1-methylbenzimidazoleHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 866254762,2,2-Trichloroethyl (1-methyl-1H-benzimidazol-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-1H-benzimidazol-2-amine (1.00 g, 6.79 mmol) and pyridine (0.646 ml, 8.15 mmol) in tetrahydrofuran (23 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.13 ml, 8.15 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 546 mg (24.9%) 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 546 mg (24.9%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-92f70778fe9c4a979cfdb9a733507750
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Linked notes

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