Water → HCID 86245090, compound

HRID 2263142Notes

Reaction equation

HRID 2263142 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17].O>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:16](=[O:17])[O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 793055-Amino-2-chloropyridineHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 86245090HCID 86245090, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloropyridine-3-amine (1.00 g, 7.78 mmol) and pyridine (0.761 ml, 9.33 mmol) in tetrahydrofuran (25 ml) was added 2,2,2-trichloroethyl chloroformate (1.29 ml, 9.33 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. Hexane was poured to the residue and a solid was collected by filtration to obtain the desired product (2.17 g, 92.0%).

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. additionHexane was poured to the residue
  7. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-b559b84a34464dae9bbe19f2b12bf3ae
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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