Chloroform → HCID 66958351, compound

HRID 1360463Notes

Reaction equation

HRID 1360463 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 18,139.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Chlorobutyl)-1-propyl-1H-pyrazole-3-carboxamide (30.95 g, 0.127 mmol) 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-b98083a4b5a2440092965966be60e72e
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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