Dichloromethane → Phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamate

HRID 891087Notes

Reaction equation

HRID 891087 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=2)[N:3]=1.ClCCl.C(N(CC)CC)C.[C:33](Cl)(=[O:41])[O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][C:33](=[O:41])[O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:18][CH:19]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 222446652-[4-(3,5-Dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylamine

Product 1

HCID 22244550Phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylamine (step 3 of Example 14, 1.36 g, 4.66 mmol), dichloromethane (30 m]L) and triethylamine (0.78 mL, 5.60 mmol) was added phenyl chlorocarbonate (0.64 mL, 5.13 mmol) slowly at room temperature. After 1 h, the mixture was poured into water and extracted with dichloromethane. The organic fraction was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with hexane/ethyl acetate (2:1) to afford 1.57 g (82%) of the title compound as white solids: MS (ESI) m/z 412 [M+H]+, 1H-NMR (CDCl3) δ 7.48-7.10 (14H, m), 5.06 (1H, br.s), 3.60-3.53 (2H, m), 2.96 (2H, t, J=6.8 Hz), 2.34 (3H, s), 2.31 (3H, s).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic fraction was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography
  5. washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-9b043c8ff33344199b19b698816dc332
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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