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

HRID 374277ノート

反応式

HRID 374277 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c5f87846b0544d01b03ba973a8882a24
出典データセット
uspto-grants-1992_11
特許番号
US05166390

反応ノート

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