Nitrite → 5-Cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester

HRID 329775

반응식

HRID 329775 반응식
Cl.[NH2:2][CH2:3][C:4]#[N:5].[C:6]([O:15][CH2:16][CH3:17])(=[O:14])/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10].[N:18]([O-])=O.[Na+].N([O-])=O>C(OCC)(=O)C>[CH2:16]([O:15][C:6]([CH:7]1[CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]([C:3]#[N:2])[N:5]=[N:18]1)=[O:14])[CH3:17]

참가 물질

6

반응물 4

HCID 946NitriteHCID 638144Diethyl fumarateHCID 11491918Aminoacetonitrile hydrochlorideHCID 23668193Sodium Nitrite

생성물 1

HCID 147663655-Cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
24 °C

실험 절차

To a 500 ml, 3-neck, round bottom flask containing a cold (0° C.) slurry of 46.26 g (0.5 mol) of aminoacetonitrile hydrochloride and 32.74 ml (0.2 mol) of diethyl fumarate in 200 ml of ethyl acetate, were added dropwise, over one hour, an aqueous solution of sodium nitrite (34.5 g of sodium nitrite dissolved in 90 ml of water). The temperature of the reaction mixture was maintained between 0° C. and 5° C. during nitrite addition and then warmed to room temperature (24° C.), where the mixture was stirred for about 3 hours. The organic layer was separated from the aqueous layer and then stirred at room temperature overnight to provide a solution of title compound dissolved in ethyl acetate.

후처리

  1. additionwere added dropwise, over one hour
  2. customThe organic layer was separated from the aqueous layer
  3. stirringstirred at room temperature overnight

출처 및 근거

ORD 기록
ord-83a2a8f18d74417bba394f8dbc005b17
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892956

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