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Hydrochloric Acid → 4-(5-Dodecyl-2-pyrimidinyl)phenyl 5-hexylthiophene-2-carboxylate

HRID 1196799
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HRID 1196799 반응식
N1C=CC=CC=1.[CH2:7]([C:19]1[CH:20]=[N:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[N:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:32]([C:38]1[S:42][C:41]([C:43](Cl)=[O:44])=[CH:40][CH:39]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].Cl>O>[CH2:32]([C:38]1[S:42][C:41]([C:43]([O:31][C:28]2[CH:27]=[CH:26][C:25]([C:22]3[N:23]=[CH:24][C:19]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:20][N:21]=3)=[CH:30][CH:29]=2)=[O:44])=[CH:40][CH:39]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 131282725-Hexylthiophene-2-carboxylic acid chlorideHCID 1360357064-(5-Dodecyl-2-pyrimidinyl)phenol

생성물 1

HCID 198962914-(5-Dodecyl-2-pyrimidinyl)phenyl 5-hexylthiophene-2-carboxylate수율 30.2%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

15 ml of pyridine was added to 0.80 g (2.36×10-3 mol) of 4-(5-dodecyl-2-pyrimidinyl)phenol, followed by cooling on an iced water bath. To the mixture, 0.54 g (2.36×10-3 mol) of 5-hexylthiophene-2-carboxylic chloride was added, followed by stirring for 5 hours at room temperature. After the reaction, the reaction mixture was poured into 100 ml of water and acidified with conc. hydrochloric acid, followed by three times of extraction with 50 ml of isopropyl ether. The organic layer was washed with water repeatedly until the washing liquid reacted neutrality, followed by drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography with the use of a hexane/ethyl acetate =10/1 mixture solvent and recrystallized from ethanol to obtain 0.38 g of a pure product (yield: 30.2%). ##STR29##

후처리

  1. temperatureby cooling on an iced water bath
  2. customAfter the reaction
  3. extractionfollowed by three times of extraction with 50 ml of isopropyl ether
  4. washThe organic layer was washed with water repeatedly until the washing liquid
  5. customreacted neutrality
  6. dry with materialby drying with anhydrous magnesium sulfate and distilling-off of the solvent
  7. customto obtain a crude product
  8. customThe crude product was purified by silica gel column chromatography with the use of a hexane/ethyl acetate =10/1 mixture solvent
  9. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-444b0639d3854c2586e0b767a1177cae
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05116530

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