Sodium ethoxide → ethyl 1-(4-chloro-1H-pyrazol-1-yl)cyclopropanecarbimidate

HRID 931148Notes

Reaction equation

HRID 931148 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[CH:6]=1.[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10](=[NH:11])[O:12][CH2:13][CH3:14])[CH2:8][CH2:9]2)[CH:6]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 898536581-(4-Chloropyrazol-1-yl)cyclopropane-1-carbonitrile

Product 1

HCID 117966385ethyl 1-(4-chloro-1H-pyrazol-1-yl)cyclopropanecarbimidate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(4-chloro-1H-pyrazol-1-yl)cyclopropanecarbonitrile (17.3 g, 103 mmol) in ethanol (50 mL) was added sodium ethoxide (prepared from 3.2 g, 139 mmol of sodium metal dissolved in 150 mL of ethanol). The reaction mixture was stirred at 70° C. for 2 h to afford ethyl 1-(4-chloro-1H-pyrazol-1-yl)cyclopropanecarbimidate which was used for the next step without further purification. An aliquot of the solution was concentrated for analysis: 1H NMR (400 MHz, CDCl3): δ 1.25 (t, 3H), 1.46 (q, 2H), 1.73 (q, 2H), 4.15 (q, 2H), 7.51 (s, 1H), 7.52 (s, 1H).

Sources & evidence

ORD record
ord-791bc05e48f644d49b4874cd539ae6aa
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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