2-n-Octyl-4-isothiazolin-3-one → N-n-Octyl-cis-3-{[1-phenyl-3-(1-methylpyrrol-2-yl)-1,3-propanedionyl]thio}acrylamide

HRID 892429

反応式

HRID 892429 の反応式
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:17])[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:36]([N:44]1[C:48](=[O:49])[CH:47]=[CH:46][S:45]1)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CN(C)C=O.O1CCCC1.Cl>[CH2:36]([NH:44][C:48](=[O:49])/[CH:47]=[CH:46]\[S:45][CH:8]([C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:17])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

参加物

7

反応物 3

HCID 335282-n-Octyl-4-isothiazolin-3-oneHCID 2724141Tetrabutylammonium Fluoride2 回HCID 198953681-(1-Methylpyrrol-2-yl)-3-phenyl-1,3-propanedione

生成物 1

HCID 86745881N-n-Octyl-cis-3-{[1-phenyl-3-(1-methylpyrrol-2-yl)-1,3-propanedionyl]thio}acrylamide収率 19%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 0.78 g (0.0034 mol) of 1-(1-methylpyrrol-2-yl)-3-phenyl-1,3-propanedione in 5 mL of N,N-dimethylformamide under nitrogen was added 3.4 mL (0.0034 mol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. After 10 min a solution of 0.73 g (0.0034 mol) of 2-n-octyl-4-isothiazolin-3-one in 5 mL of N,N-dimethylformamide was added. After 12 h another 3.4 mL of the 1M tetrabutylammonium fluoride solution was added. After 12 h the reaction mixture was diluted with 10% aqueous hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were washed several times with water, once with brine, and dried over magnesium sulfate. Removal of solvents and recrystallization of the crude product from ethyl acetate/hexane gave 0.28 g (19% yield) of N-n-Octyl-cis-3-{[1-phenyl-3-(1-methylpyrrol-2-yl)-1,3-propanedionyl]thio}acrylamide as a white solid, m.p. 131°-132° C. See Table 1.

後処理

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed several times with water
  3. dry with materialonce with brine, and dried over magnesium sulfate
  4. customRemoval of solvents and recrystallization of the crude product from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-5726f35de72e4be088d74d4981417cbc
出典データセット
uspto-grants-1992_06
特許番号
US05118681

関連ノート

読み込み中…