Pentanoic Acid → HCID 19770585, compound

HRID 1589728Notes

Reaction equation

HRID 1589728 reaction equation
[CH2:1]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=2)=[N:14][N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:24](O)(=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH2:1]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[C:18]([F:23])[CH:17]=2)=[N:14][N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 7991Pentanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 135590743HCID 135590743, compound

Product 1

HCID 19770585HCID 19770585, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 ml of dichloromethane was added to a mixture of 2.0 g (5.94 mM) of 2-decyl-5-(3-fluoro-4-hydroxyphenyl)-1,3,4-thiadiazole and 0.61 g (5.97 mM) of pentanoic acid. Under stirring at room temperature, 1.21 g (5.86 mM) of N,N'-dicyclohexylcarbodiimide (DCC) and 0.05 g of 4-pyrrolidinopyridine were successively added to the above mixture, followed by stirring for 19 hours at room temperature. After the reaction, precipitated N,N'-dicyclohexylurea was recovered by filtration, washed with dichloromethane and added to the filtrate. The resultant dichloromethane solution was subjected to distillation under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: benzene) and recrystallized from ethanol to obtain 1.40 g of 2-decyl-5-(3-fluoro-4-pentanoyloxyphenyl)-1,3,4-thiadiazole (Yield: 56.9%). ##STR132##

Workup

  1. stirringby stirring for 19 hours at room temperature
  2. customAfter the reaction
  3. customprecipitated N,N'-dicyclohexylurea
  4. filtrationwas recovered by filtration
  5. washwashed with dichloromethane
  6. additionadded to the filtrate
  7. distillationThe resultant dichloromethane solution was subjected to distillation under reduced pressure
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography (eluent: benzene)
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a504651866174572b57f8525e9c50eaf
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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