Ammonia → HCID 84079539, compound

HRID 2277590Notes

Reaction equation

HRID 2277590 reaction equation
C[O:2][C:3](=O)[NH:4][CH2:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)([CH3:8])[CH3:7].N>>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[C:3](=[O:2])[NH:4][CH2:5][C:6]2([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86685924HCID 86685924, compound

Product 1

HCID 84079539HCID 84079539, compoundYield 20%

Conditions

Temperature
120 °C

Procedure

Under N2 protection, a mixture of [2-(3-chloro-phenyl)-2-methyl-propyl]-carbamic acid methyl ester (1.84 g, 7.63 mmol) and PPA (polyphosphoric acid) (8 g) in a 100 mL round bottom flask was stirred at 120° C. for 2 hours. After cooling to room temperature, the mixture was treated with ice-water and aq. ammonia solution to adjust the pH to 8. After extraction with ethyl acetate, 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 (0.32 g, 20%) as a white solid. MS: 210.1 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionAfter extraction with ethyl acetate
  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-7dc1b53cf698407189ef4ccc035d53b0
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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