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Potassium Carbonate → N,N'-bis(2-chloro-5-thiazolylmethyl)-N"-nitroguanidine

HRID 1275363
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HRID 1275363 반응식
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9](=[N:12][N+:13]([O-:15])=[O:14])SC)=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[S:24][C:25]([CH2:28][NH2:29])=[CH:26][N:27]=1>C(#N)C>[Cl:22][C:23]1[S:24][C:25]([CH2:28][NH:29][C:9]([NH:8][CH2:7][C:4]2[S:3][C:2]([Cl:1])=[N:6][CH:5]=2)=[N:12][N+:13]([O-:15])=[O:14])=[CH:26][N:27]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136331499N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea

생성물 1

HCID 135827986N,N'-bis(2-chloro-5-thiazolylmethyl)-N"-nitroguanidine수율 13.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 1 g N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea, 560 mg potassium carbonate, 400 mg cuprous chloride and 12 ml acetonitrile was added 610 mg of 2-chloro-5-(aminomethyl)thiazole and the mixture was stirred for 1 hour under reflux. Thereafter, the reaction mixture was concentrated, then water was added to the resultant solids, followed by stirring thoroughly. Thereafter, the solids were collected by filtration and purified by column chromatography [eluent: dichloromethane-methanol (10:1)] to afford 191 mg of N,N'-bis(2-chloro-5-thiazolylmethyl)-N"-nitroguanidine (compound No.39) as a white powder, mp 217-218° C.

후처리

  1. temperatureunder reflux
  2. concentrationThereafter, the reaction mixture was concentrated
  3. additionwater was added to the resultant solids
  4. stirringby stirring thoroughly
  5. filtrationThereafter, the solids were collected by filtration
  6. custompurified by column chromatography [eluent: dichloromethane-methanol (10:1)]

출처 및 근거

ORD 기록
ord-ec03cfea332e4b47aea7ffbfb6603369
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06160126

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