Chloroform → HCID 66958351, compound

HRID 2283787Notes

Reaction equation

HRID 2283787 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][CH2:12][CH3:13])[N:9]=[C:8]([C:14]([NH2:16])=O)[CH:7]=1.P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][CH2:12][CH3:13])[N:9]=[C:8]([C:14]#[N:16])[CH:7]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 66958914HCID 66958914, compound

Product 1

HCID 66958351HCID 66958351, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Chlorobutyl)-1-propyl-1H-pyrazole-3-carboxamide (30.95 g, 0.127 mol) in toluene (250 mL) was treated with phosphorous oxychloride (24.86 mL, 0.267 mol). The solution was heated at reflux for 40 minutes. The reaction was worked-up as described in Part D of Examples 37-39, with the exception that chloroform was used in place of methyl tert-butyl ether, to yield 5.20 g of 5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile as an oil. 1H-NMR (300 MHz, CDCl3) δ 6.43 (s, 1H), 4.04 (t, J=7.3 Hz, 2H), 3.62-3.53 (m, 2H), 2.70-2.58 (m, 2H), 1.94-1.76 (m, 6H), 0.93 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 40 minutes

Sources & evidence

ORD record
ord-ad2f3130b5124b728eb2b0292ff31d58
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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