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

HRID 1196799Notes

Reaction equation

HRID 1196799 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-444b0639d3854c2586e0b767a1177cae
Source dataset
uspto-grants-1992_05
Patent number
US05116530

Reaction notes

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