Sodium Carbonate → 5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

HRID 1984352

Reaction equation

HRID 1984352 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]O)=[CH:6][C:5]([C:13]([NH2:15])=O)=[N:4]1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([C:13]#[N:15])[CH:6]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 669587601-ethyl-5-(4-hydroxybutyl)-1H-pyrazole-3-carboxamide

Product 1

HCID 669589675-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

Conditions

Temperature
0 °C

Procedure

A modification of the method described in Part E of Examples 1-4 was used to treat 1-ethyl-5-(4-hydroxybutyl)-1H-pyrazole-3-carboxamide (18.2 g, 86.1 mmol) with phosphorous oxychloride (60 mL). The reaction was heated for three hours before cooling to 0° C. and pouring into ice water. The mixture was adjusted to pH 12 with the addition of 2 N aqueous sodium carbonate and extracted with chloroform. The combined extracts were passed through a layer of silica gel (eluting first with chloroform and then with 1:1 hexane/ethyl acetate to provide 10.8 g of 5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile as a dark oil.

Workup

  1. temperatureThe reaction was heated for three hours
  2. extractionextracted with chloroform
  3. washeluting first with chloroform

Sources & evidence

ORD record
ord-4c347ddfbb054590b7905470dd8abe46
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Linked notes

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