Ethyl cyanoacetate → HCID 18688664, compound

HRID 1873229Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:24].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:23]([CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])#[N:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Diethyl 2-(3-chloro-4-nitrophenyl)-2-methylmalonate (119 mg, 0.36 mmol.), ethyl cyanoacetate (81 mg, 0.72 mmol.), powdery potassium carbonate (119 mg, 0.86 mmol.), and dimethyl sulfoxide (1 mL) were mixed and stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, and washed with diethyl ether after addition of water. The aqueous portion was made acidic by addition of 6N hydrochloric acid, and extracted with diethyl ether. The ether portion was washed successively with water and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off to give 133 mg (yield: 92%) of the desired compound as a yellow oil.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with diethyl ether
additionafter addition of water
additionThe aqueous portion was made acidic by addition of 6N hydrochloric acid
extractionextracted with diethyl ether
washThe ether portion was washed successively with water
dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-a18f04806da7495b8871167670e70da0
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06111115

Reaction notes

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