Pyridine → 2,2,2-Trichloroethyl 4-bromo-5-methylisoxazol-3-ylcarbamate

HRID 1744104Notes

Reaction equation

HRID 1744104 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[C:5]([CH3:8])[O:4][N:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.ClCCl>[Br:7][C:6]1[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[N:3][O:4][C:5]=1[CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 27744644-Bromo-5-methyl-1,2-oxazol-3-amine

Product 1

HCID 222357552,2,2-Trichloroethyl 4-bromo-5-methylisoxazol-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-amino-4-bromo-5-methylisoxazole (2.58 g, 14.6 mmol) and DMAP (893 mg, 7.3 mmol) in 60 mL dichloromethane at −78° C. was added pyridine (6 ml, 74.1 mmol) followed by 2,2,2-trichloroethyl chloroformate (8 ml, 58 mmol). The reaction was allowed to warm to room temperature while stirring over ca. 4 hours. Ice water was added, the aqueous phase neutralized with saturated aq. NaHCO3, and the product extracted with ether (3×), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (20% ethyl acetate/hexane) to afford 2,2,2-trichloroethyl 4-bromo-5-methylisoxazol-3-ylcarbamate.

Workup

  1. extractionthe product extracted with ether (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5c84ee7143104145afdca445389f7a2d
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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