Water → N-cyclododecyl-cis-3-(acetylthio)acrylamide

HRID 1463556노트

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HRID 1463556 반응식
[C:1]([S:4]/[CH:5]=[CH:6]\[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[CH:10]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C.O>ClCCl>[CH:10]1([NH:22][C:7](=[O:8])/[CH:6]=[CH:5]\[S:4][C:1](=[O:3])[CH3:2])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

6

반응물 4

HCID 962WaterHCID 2897CyclododecanamineHCID 8471TriethylamineHCID 86746380cis-3-(Acetylthio)propenoyl chloride

생성물 1

HCID 86746381N-cyclododecyl-cis-3-(acetylthio)acrylamide수율 10%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred, cooled (0° C.) solution of 3.0 g (0.0162 mol) of cis-3-(acetylthio)propenoyl chloride in 30 ml of dichloromethane under nitrogen was added dropwise 2.98 g (0.0163 mol) of cyclododecylamine as a solution in 30 ml of dichloromethane. After 15 min, 2.27 ml (0.0163 mol) of triethylamine was added dropwise. After 12 h the reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic layers were washed with water, brine, and dried over magnesium sulfate. Filtration and removal of solvents gave 4.5 g of a 2:1 mixture of cis and trans isomers as a tan solid. Purification by flash column chromatography (Merck 60® silica gel, ethyl acetate/hexane eluant) gave 0.5 g (10% yield) of N-cyclododecyl-cis-3-(acetylthio)acrylamide as a white powder where NMR is reported in Table 2.

후처리

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and removal of solvents
  5. customgave
  6. addition4.5 g of a 2:1 mixture of cis and trans isomers as a tan solid
  7. customPurification by flash column chromatography (Merck 60® silica gel, ethyl acetate/hexane eluant)

출처 및 근거

ORD 기록
ord-cabb79b40cf741a497d9078ef71e8a16
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300672

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