1-Octanol → HCID 19100387, compound

HRID 2254495Notes

Reaction equation

HRID 2254495 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:27](O)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:27]([O:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)=[O:3])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 9571-OctanolHCID 10868DicyclohexylcarbodiimideHCID 19100372HCID 19100372, compound

Product 1

HCID 19100387HCID 19100387, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 0.30 g (0.82 mM) of 2-(p-carboxyphenyl)-6-octylbenzothiazole, 0.12 g (0.92 mM) of octanol and 10 ml of methylene chloride were added, followed by addition of 0.17 g (0.82 mM) of N,N'-dicyclohexylcarbodiimide (DCC) and 0.02 g of 4-dimethylaminopyridine under stirring at room temperature and further stirring for 6 hours at room temperature. After the reaction, the resultant N,N'-dicyclohexylurea was recovered by filtration, followed by washing with methylene chloride to be added to the filtrate. The solvent of the resultant filtrate was distilled-off under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene), followed by recrystallization from a mixture solvent of toluene/methanol to obtain 0.20 g of 2-(p-octyloxycarbonylphenyl)-6-octylbenzothiazole (Yield: 51.1%). ##STR196##

Workup

  1. stirringfurther stirring for 6 hours at room temperature
  2. customAfter the reaction
  3. filtrationthe resultant N,N'-dicyclohexylurea was recovered by filtration
  4. washby washing with methylene chloride
  5. additionto be added to the filtrate
  6. customto obtain a residue
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  8. customfollowed by recrystallization from a mixture solvent of toluene/methanol

Sources & evidence

ORD record
ord-1465244ca36444f6841afe523cf2a34a
Source dataset
uspto-grants-1993_08
Patent number
US05236619

Reaction notes

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