Water → 3-Imino-2-(1-methyl-3-phenylthioureido)isoindolin-1-one

HRID 1065732노트

반응식

HRID 1065732 반응식
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6])#[N:2].[CH3:12][N:13]([C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[S:16])[NH2:14].N1C=CC=CC=1.O>C(COC)OC>[NH:2]=[C:1]1[C:3]2[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[N:14]1[N:13]([CH3:12])[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[S:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 1196812-Cyanobenzoyl chlorideHCID 853583Sbb062267

생성물 1

HCID 128501933-Imino-2-(1-methyl-3-phenylthioureido)isoindolin-1-one수율 166.9%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

A solution of crude 2-cyanobenzoylchloride (2.2 g; 0.013 mole) in 20 ml of dimethoxyethane was added dropwise to a solution of 2-methyl-4-phenylthiosemicarbazide 0.35 g; 0.013 mole) and pyridine (1.1 g; 0.013 mole) in 35 ml of dimethoxyethane. The resulting red solution was allowed to stir at room temperature overnight. The reaction mixture was poured into a large volume of water to give a reddish gummy precipitate. The water was decanted and the gummy material dissolved in a small amount of ethyl acetate. Upon standing a solid crystallized from solution. Filtration gave 1 g of the desired product, mp: 165-167. The IR and NMR spectra were consistent with the cyclic tautomer structure, as illustrated in the foregoing reaction scheme. Under basic conditions, as in the exemplified synthesis procedure, existence of the tautomeric ortho-cyanobenzoyl compound is probably negligible. It is conceivable, however, that in some chemical environments the tautomeric form can be detected, or that reaction products derived from the tautomeric form will be produced when identification by preparation of chemical derivatives is attempted.

후처리

  1. customto give a reddish gummy precipitate
  2. customThe water was decanted
  3. dissolutionthe gummy material dissolved in a small amount of ethyl acetate
  4. customcrystallized from solution
  5. filtrationFiltration

출처 및 근거

ORD 기록
ord-08874752cd9e4b5daba7ae471172c9bc
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04331467

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