Sodium Hydroxide → HCID 22244667, compound

HRID 891129Notes

Reaction equation

HRID 891129 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[C:12]([CH3:24])=[N:11]2)=[CH:6][CH:5]=1.[OH-:25].[Na+]>OS(O)(=O)=O>[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]([NH2:20])=[O:25])[C:12]([CH3:24])=[N:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22244703HCID 22244703, compound

Product 1

HCID 22244667HCID 22244667, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-{1-[4-(2-chloroethyl)phenyl]-3,5-dimethyl-1H-pyrazol-4-yl}benzonitrile (step 2, 2.62 mmol) in conc. H2SO4 was heated at 80° C. for 5 h. It was neutralized by 5 M NaOH aq. and extracted with dichloromethane. Organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure to afford 780 mg (84%) of the title compound as yellow solids: MS (ESI) m/z 354 [M+H]+, 1H-NMR (CDCl3) δ 7.80-7.36 (8H, m), 3.75 (2H, t, J=7.2 Hz), 3.14 (2H, t, J=7.2 Hz), 2.33 (3H, s), 2.31 (3H, s).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialOrganic phase was dried over Na2SO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cc4a0def377641cb82679322387f4d21
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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