Ethanol hydrochloride → 2-chloro-4-(4-chloro-1H-pyrazol-5-yl)benzonitrile hydrochloride

HRID 872757Notes

Reaction equation

HRID 872757 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[Cl:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.C(O)C>>[ClH:1].[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[Cl:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 671725012-chloro-4-(4-chloro-1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 706538202-chloro-4-(4-chloro-1H-pyrazol-5-yl)benzonitrile hydrochlorideYield 18%

Procedure

2-chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile (12.0 g, 41.7 mmol) was dissolved in acetic acid (20 ml) and sodium hypochlorite solution (29.0 ml, 416 mmol) was added. The reaction mixture was stirred at RT overnight. Further again, acetic acid (120 ml) and sodium hypochlorite solution (14 ml) were added and the mixture was stirred at RT overnight. The precipitate was filtrated and washed with water and DCM. The precipitate was dried in vacuum 40° C. overnight to yield 5.8 grams of 2-chloro-4-(4-chloro-1H-pyrazol-5-yl)benzonitrile. The mixture of 2-chloro-4-(4-chloro-1H-pyrazol-5-yl)benzonitrile (5.8 g, 24.36 mmol) and 10% HCl/ethanol solution (167 ml, 365 mmol) was stirred for 2 h at RT and the precipitate was filtrated and washed with water. The precipitate was silted up with ethanol to yield 4.0 g of the raw material. The product was purified with Flash-chromatography to yield total 18% of the title compound. 1H NMR (400 MHz; d6-DMSO): δ 8.05 (m, 2H), 8.16 (m, 2H).

Workup

  1. filtrationthe precipitate was filtrated
  2. washwashed with water
  3. customto yield 4.0 g of the raw material
  4. customThe product was purified with Flash-chromatography

Sources & evidence

ORD record
ord-50f5ab72bc4e4ad2a641a1c3fed7a166
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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