Dicyclohexylcarbodiimide → 2,3-Dicyano-4-hexyloxyphenyl 5-hexylthiophene-2-carboxylate

HRID 892383

반응식

HRID 892383 반응식
[CH2:1]([C:7]1[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:15]([O:21][C:22]1[CH:28]=[CH:27][C:25](O)=[C:24]([C:29]#[N:30])[C:23]=1[C:31]#[N:32])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CC=CN=2)CCCC1>C1COCC1>[CH2:1]([C:7]1[S:11][C:10]([C:12]([O:14][C:25]2[CH:27]=[CH:28][C:22]([O:21][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:23]([C:31]#[N:32])[C:24]=2[C:29]#[N:30])=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 131282695-Hexyl-2-thiophenecarboxylic acidHCID 150066893-(Hexyloxy)-6-hydroxybenzene-1,2-dicarbonitrile

생성물 1

HCID 150066902,3-Dicyano-4-hexyloxyphenyl 5-hexylthiophene-2-carboxylate수율 53.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

0.50 g (2.36 mM) of 5-hexylthiophene-2-carboxylic acid (M.W.: 212), 0.58 g (2.36 mM) of 2,3-dicyanohydroquinone monohexyl ether (M.W.: 244) and 20 ml of THF were mixed and stirred. To the mixture, 0.49 g (2.36 mM) of dicyclohexylcarbodiimide (M.W.: 206) and 0.05 g of pyrrolidinopyridine were added, followed by stirring overnight at room temperature. After the reaction, the reaction mixture was subjected to filtration and the filtrate was subjected to distillation to obtain a crude product. The crude product was purified by silica gel column chromatography with the use of benzene and recrystallized from ethanol to obtain 0.55 g of an objective product (yield: 53.4%).

후처리

  1. stirringby stirring overnight at room temperature
  2. customAfter the reaction
  3. filtrationthe reaction mixture was subjected to filtration
  4. distillationthe filtrate was subjected to distillation
  5. customto obtain a crude product
  6. customThe crude product was purified by silica gel column chromatography with the use of benzene
  7. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-cafb66d079024aa8b5340a302514b76d
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05118441

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