Heptanoyl chloride → HCID 19907941, compound

HRID 1534764Notes

Reaction equation

HRID 1534764 reaction equation
[C:1](Cl)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:10]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:23][C:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[C:32]([OH:37])[CH:33]=4)[CH:28]=3)=[N:25][N:26]=2)=[CH:18][CH:17]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>N1C=CC=CC=1>[CH2:10]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:23][C:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[C:32]([O:37][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:33]=4)[CH:28]=3)=[N:25][N:26]=2)=[CH:18][CH:17]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 17313Heptanoyl chlorideHCID 136058235HCID 136058235, compound

Product 1

HCID 19907941HCID 19907941, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 30 ml-round-bottomed flask, 0.30 g (0.77 mM) of 2-(4-hexylphenyl)-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole was dissolved in 5 ml of pyridine. To the solution, 0.20 ml (1.29 mM) of heptanoyl chloride was added dropwise under cooling with an iced water bath and stirring. After the addition, the iced water bath was removed. Then, the mixture was stirred for 7 hours at room temperature and left standing overnight at room temperature. The resultant mixture was poured into 100 ml of iced water to precipitate a crystal. The crystal was recovered by filtration, washed with water and dissolved in toluene under heating, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene-acetone) to obtain 0.27 g of 2-(4-hexylphenyl)-5-(6-heptanoyloxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 69.8%) ##STR39##

Workup

  1. temperatureunder cooling with an iced water bath
  2. additionAfter the addition
  3. customthe iced water bath was removed
  4. stirringThen, the mixture was stirred for 7 hours at room temperature
  5. waitleft
  6. additionThe resultant mixture was poured into 100 ml of iced water
  7. customto precipitate a crystal
  8. filtrationThe crystal was recovered by filtration
  9. washwashed with water
  10. dissolutiondissolved in toluene
  11. temperatureunder heating
  12. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
  13. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  14. customrecrystallized from a mixture solvent (toluene-acetone)

Sources & evidence

ORD record
ord-b3524fd4b4fd4a8cba0718ee8ba5c575
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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