Methyl fluorosulfate → N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate

HRID 1649046

反応式

HRID 1649046 の反応式
[CH3:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=O.FS(OC)(=O)=O.[C:14]1([NH:20][C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[NH:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C(Cl)Cl.C(O)(C)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH3:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=[N:22][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[N:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

8

反応物 5

HCID 9870Methyl fluorosulfateHCID 14798Sodium HydroxideHCID 298312-Oxazolidinone, 3-methyl-HCID 444972Fumaric AcidHCID 178511988HCID 178511988、化合物

生成物 1

HCID 70510611N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-methyloxazolidin-2-one, 2.02 g (0.02 mole), in dry methylene chloride under dry nitrogen is added 2.28 g (0.02 mole) of methyl fluorosulfonate in one portion. After stirring 3 hrs, 0.02 mole of N-phenyl-1-pyrrolidinecarboximidamide free base in dry methylene chloride is added. After stirring at room temperature overnight, the solution is shaken with excess cold 3 N NaOH. The organic layer is separated and dried over K2CO3, filtered, and the solvent removed in vacuo to afford the crude base. Addition of an equimolar amount of fumaric acid to a solution of the free base in isopropanol, followed by recrystallization from isopropanol/ether affords pure N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate; m.p. 160°-162° C.

後処理

  1. stirringAfter stirring at room temperature overnight
  2. customThe organic layer is separated
  3. dry with materialdried over K2CO3
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto afford the crude base
  7. customfollowed by recrystallization from isopropanol/ether

出典と根拠

ORDレコード
ord-e962d691496846a3a53882cbbe5133fd
出典データセット
uspto-grants-1983_11
特許番号
US04414211

関連ノート

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