Heptanoic Acid → HCID 23354796, compound

HRID 234569Notes

Reaction equation

HRID 234569 reaction equation
[CH2:1]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:14][N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:23](O)(=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].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:17]=[CH:18][C:19]([O:22][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:21]=2)=[CH: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 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 233547574-(2-Decyl-1,3-thiazol-5-yl)phenol

Product 1

HCID 23354796HCID 23354796, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 ml-round-bottomed flask, 0.60 g (1.89 mM) of 2-decyl-5-(4-hydroxyphenyl)thiazole, 0.28 ml (1.97 mM) of heptanoic acid and 15 ml of dichloromethane were placed and mixed. To the solution, 0.39 g (1.89 mM) of N,N'-dicyclohexylcarbodiimide and 0.03 g of 4-pyrrolidinopyridine were successively added under stirring at room temperature, followed by further stirring for 2 hours at room temperature. After stirring, the mixture was left standing overnight at room temperature to precipitate N,N'-dicyclohexylurea. The resultant N,N'-dicyclohexylurea was filtered off and the solvent of the filtrate was distilled-off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from acetone to obtain 0.62 g of 2-decyl-5-(4-heptanoyloxyphenyl)thiazole (Yield: 76.4%). ##STR92##

Workup

  1. additionmixed
  2. stirringby further stirring for 2 hours at room temperature
  3. stirringAfter stirring
  4. waitthe mixture was left
  5. customto precipitate N,N'-dicyclohexylurea
  6. filtrationThe resultant N,N'-dicyclohexylurea was filtered off
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-3c7918ece9b745418811bc2be009de47
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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