18-Crown-6 → [1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

HRID 1449139노트

반응식

HRID 1449139 반응식
Br[CH2:2][CH2:3][N:4]([C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:20]=[N+:21]=[N-:22].CN(C)C(=[NH2+])N(C)C.C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[N:20]([CH2:2][CH2:3][N:4]([C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:21]=[N-:22]

참가 물질

5

반응물 3

HCID 2855718-Crown-6HCID 86736837[1-(2-Bromoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl esterHCID 178484365HCID 178484365, 화합물

생성물 1

HCID 86736838[1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

11 g. of the ethyl ester product from part (c) are added to acetone along with 5.7 g. of tetramethylguanidinium azide and 0.05 g. of 18-Crown-6. The mixture is refluxed for eight hours. After distilling off the solvent, the reaction mixture is stirred with 50 ml. of methylene chloride. The organic phase, after drying and concentrating, leaves an oil which crystallizes in the form of white crystals upon the addition of a small amount of isopropanol to yield [1-(2-azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester; m.p. 59°-61°.

후처리

  1. temperatureThe mixture is refluxed for eight hours
  2. distillationAfter distilling off the solvent
  3. customThe organic phase, after drying
  4. concentrationconcentrating
  5. customleaves an oil which
  6. customcrystallizes in the form of white crystals upon the addition of a small amount of isopropanol

출처 및 근거

ORD 기록
ord-614aac344621482ab97a84b8bbaff094
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04189482

반응 노트

불러오는 중…