Chlorosuccinimide → (4-Chloro-5-cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester

HRID 450306Notes

Reaction equation

HRID 450306 reaction equation
[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[CH:14]=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:12][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Cl:26])C(=O)C1>CC(O)=O.O.C(OCC)(=O)C>[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[C:14]([Cl:26])=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:12][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 59394551(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester

Product 1

HCID 59394659(4-Chloro-5-cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
79 °C

Procedure

(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester (0.25 g, 1.024 mmol) is dissolved in AcOH (7.31 mL) and NCS (0.205 g, 1.53 mmol) is added and the reaction is heated to 79° C. for 2 hours. The reaction is cooled to room temperature and diluted with water and ethyl acetate. The organic layer is washed with 500 mL of water to remove the acid. The organic layer is dried (sodium sulfate) and concentrated to an oil (352 mg) to obtain the title compound that is used without further purification. MS (ESI) m/z 279.00 (M+1).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. washThe organic layer is washed with 500 mL of water
  3. customto remove the acid
  4. dry with materialThe organic layer is dried (sodium sulfate)
  5. concentrationconcentrated to an oil (352 mg)

Sources & evidence

ORD record
ord-54414dc2e29d4c5e829064fee508088a
Source dataset
uspto-grants-2013_07
Patent number
US08486954B2

Reaction notes

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