Pyridine → HCID 67493799, compound

HRID 1920725Notes

Reaction equation

HRID 1920725 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH:7]([CH2:9][CH3:10])[CH3:8])[CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19]>C(Cl)Cl>[Cl:23][C:22]([Cl:25])([Cl:24])[CH2:21][O:20][C:18](=[O:19])[NH:1][C:2]1[O:6][N:5]=[C:4]([CH:7]([CH2:9][CH3:10])[CH3:8])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 131682125-Isoxazolamine,3-(1-methylpropyl)-(9CI)

Product 1

HCID 67493799HCID 67493799, compoundYield 140.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-3-sec-butylisoxazole (500 mg; 3.57 mmol; 1 equiv.) and pyridine (0.58 mL; 7.13 mmol; 2 equiv.) in DCM (30 mL) was added 0.74 mL (5.35 mmol; 1.5 equiv.) of 2,2,2-trichloroethyl chloroformate dropwise. The reaction mixture was stirred overnight at room temperature, then diluted with DCM, and washed sequentially with water, 1N HCL aqueous solution, saturated aqueous NaHCO3 solution and brine. The organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue, 1.58 g of (3-sec-Butyl-isoxazol-5-yl)-carbamic acid 2,2,2-trichloro-ethyl ester was isolated as a pale yellow oil, and used as is in the next step.

Workup

  1. washwashed sequentially with water, 1N HCL aqueous solution, saturated aqueous NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-31a1454daaa6444d8db40acfc82c5087
Source dataset
uspto-grants-2012_05
Patent number
US08173638B2

Reaction notes

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