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

반응식

HRID 892429 반응식
[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]

참가 물질

7

반응물 3

HCID 335282-n-Octyl-4-isothiazolin-3-oneHCID 2724141Tetrabutylammonium Fluoride2회HCID 198953681-(1-Methylpyrrol-2-yl)-3-phenyl-1,3-propanedione

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5726f35de72e4be088d74d4981417cbc
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05118681

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