Ammonia → HCID 84079540, compound

HRID 2277588Notes

Reaction equation

HRID 2277588 reaction equation
C[O:2][C:3](=O)[NH:4][CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)[CH3:7].N>>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[C:3](=[O:2])[NH:4][CH2:5][CH:6]2[CH3:7]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86685923HCID 86685923, compound

Product 1

HCID 84079540HCID 84079540, compoundYield 20.1%

Conditions

Temperature
120 °C

Procedure

Under N2 protection, a mixture of [2-(3-chloro-phenyl)-propyl]-carbamic acid methyl ester (3.0 g, 13.2 mmol) and PPA (polyphosphoric acid) (10 g) in a 100 mL flask was stirred at 120° C. for 2 hours. After cooling to room temperature, the reaction mixture was treated with ice-water and aqueous ammonia solution to adjust the pH to 8. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo. The crude product formed was further washed with ether to give the title compound (0.52 g, 20%) as a white solid. MS: 196.1 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customThe crude product formed
  8. washwas further washed with ether

Sources & evidence

ORD record
ord-c76df560d2ff42979cf70383aa659fdf
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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