Water → HCID 178522736, compound

HRID 2263129Notes

Reaction equation

HRID 2263129 reaction equation
[NH:1]1[C:5]([NH2:6])=[N:4][N:3]=[N:2]1.N1C=CC=CC=1.Cl[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15].O>O1CCCC1>[NH:1]1[C:5]([NH:6][C:14](=[O:15])[O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[N:4][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 178509299HCID 178509299, compound

Product 1

HCID 178522736HCID 178522736, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-tetrazole-5-amine (1.00 g, 11.8 mmol) and pyridine (1.15 ml, 14.1 mmol) in tetrahydrofuran (39 ml) was added 2,2,2-trichloroethyl chloroformate (1.95 ml, 14.1 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture and the mixture 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. To the residue was added hexane and a solid was collected by filtration to obtain the desired product (1.29 g, 42.1%).

Workup

  1. temperaturecooling
  2. extractionthe mixture 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. additionTo the residue was added hexane
  7. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-2b79f6caed7440b78b0c9601df0e9208
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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