Hydrochloric Acid → 4-(5-Hexyl-2-pyrimidinyl)phenyl 5-dodecylthiophene-2-carboxylate

HRID 1196805Notes

Reaction equation

HRID 1196805 reaction equation
N1C=CC=CC=1.[CH2:7]([C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:26]([C:38]1[S:42][C:41]([C:43](Cl)=[O:44])=[CH:40][CH:39]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].Cl>O>[CH2:26]([C:38]1[S:42][C:41]([C:43]([O:25][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[N:15]=[CH:14][C:13]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:18][N:17]=3)=[CH:24][CH:23]=2)=[O:44])=[CH:40][CH:39]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 30922104-(5-Hexyl-2-pyrimidinyl)phenolHCID 149850915-Dodecylthiophene-2-carboxylic chloride

Product 1

HCID 198962974-(5-Hexyl-2-pyrimidinyl)phenyl 5-dodecylthiophene-2-carboxylateYield 50.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 ml of pyridine was added to 0.49 g (1.93×10-3 mol) of 4-(5-hexyl-2-pyrimidinyl)phenol, followed by cooling on an iced water bath. To the mixture, 0.61 g (1.93×10-3 mol) of 5-dodecylthiophene-2-carboxylic chloride was added, followed by stirring for 4.5 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 reached 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 an ethanol/ethyl acetate mixture solvent to obtain 0.52 g of a pure product (yield: 50.5%). ##STR32##

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. dry with materialby drying with anhydrous magnesium sulfate and distilling-off of the solvent
  6. customto obtain a crude product
  7. customThe crude product was purified by silica gel column chromatography with the use of a hexane/ethyl acetate (=10/1) mixture solvent
  8. customrecrystallized from an ethanol/ethyl acetate mixture solvent

Sources & evidence

ORD record
ord-39dd39575b4e47c8977018af736da6e5
Source dataset
uspto-grants-1992_05
Patent number
US05116530

Reaction notes

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