Phenylacetyl chloride → HCID 66865174, compound

HRID 1629967Notes

Reaction equation

HRID 1629967 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH2:14][NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CCN(C(C)C)C(C)C.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH2:14][N:13]([C:32](=[O:33])[CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 21332725HCID 21332725, compound

Product 1

HCID 66865174HCID 66865174, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A scintillation vial equipped with a stir bar was charged with 3-(3,4-dimethoxy-phenyl)-4,5-dihydro-1H-pyrazole (412 mg, 2 mmol), Hunigs base (1 mL, 6 mmol) and dry CH2Cl2 (10 mL). To this mixture was added phenyl-acetyl chloride, (0.27 mL, 2 mmol) and the reaction was stirred at RT for 3 h. LC-MS indicated consumption of SM. The mixture was diluted with CH2Cl2 (50 mL) and added to water (50 mL). The phases were separated and the CH2Cl2 phase was washed with saturated Na2CO3, (50 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was purified using a 40 g silica cartridge eluting with heptane-EtOAc, gradient 0 to 100% EtOAc. Amount obtained: 123 mg, 0.37 mmol, 19% yield. LC-MS (ESI) m/e 325 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.21 (t, J=10.03 Hz, 2H) 3.94 (s, 3H) 3.98 (s, 3H) 4.04 (t, J=10.03 Hz, 2H) 4.11 (s, 2H) 6.90 (d, J=8.35 Hz, 1H) 7.16 (dd, J=8.27, 1.88 Hz, 1H) 7.21-7.26 (m, 1H) 7.31 (t, J=7.42 Hz, 2H) 7.40-7.44 (m, 3H).

Workup

  1. customA scintillation vial equipped with a stir bar
  2. customconsumption of SM
  3. additionThe mixture was diluted with CH2Cl2 (50 mL)
  4. additionadded to water (50 mL)
  5. customThe phases were separated
  6. washthe CH2Cl2 phase was washed with saturated Na2CO3, (50 mL)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe material was purified
  10. washeluting with heptane-EtOAc, gradient 0 to 100% EtOAc
  11. customAmount obtained

Sources & evidence

ORD record
ord-453b6b7b40514a54977ae39224942bb8
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

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